Method for synthesizing chiral beta-hydroxy acid ester compound

Abstract

A method for synthesizing a chiral -hydroxy acid ester compound is disclosed. The method includes the steps of: using an aldehyde compound and a monoalkyl malonate as raw materials, using a metal and a chiral ligand as a catalyst to make the raw materials be directly and fully reacted in an organic solvent and form a reaction solution, and separating and purifying the reaction solution to obtain the highly stereoselective -hydroxy acid ester compound. The beneficial effects are mainly embodied in: 1. simple operation; 2. rapidly constructing a highly stereoselective -hydroxy acid ester skeleton structure molecule; 3. high reaction yield and good stereoselectivity. Therefore, the invention has high basic research significance, industrial production value and social economic benefit.

Claims

1. A method for synthesizing a chiral -hydroxy acid ester compound, comprising the steps of: using an aldehyde compound and a monoalkyl malonate as raw materials; using a metal compound, an organic acid salt and a chiral ligand as a catalyst to make the raw materials carry out decarboxylation aldol addition reaction in an organic solvent; performing separation and purification to obtain a chiral -hydroxy acid ester compound after the reaction is completed, wherein the chiral -hydroxy acid ester compound has the structural formula as below: ##STR00040## wherein said aldehyde compound has the structural formula as below:
R.sup.1CHO wherein said monoalkyl malonate has the structural formula as below: ##STR00041## wherein said R.sup.1 is selected from one of the group consisting of an alkyl group, a substituted phenyl group or an aryl group having a fluorine, a chlorine, a bromine, a nitro group, an alkyl group and an alkoxy group; wherein said R.sup.2 is selected from one of the group consisting of a methyl, an ethyl, a propyl, a butyl, an isopropyl and a tert-butyl; wherein said organic solvent used is an organic solvent that does not react with reactants and products.

2. The method according to claim 1, wherein said organic solvent is selected from one or a combination of dichloromethane, ethyl acetate, tetrahydrofuran, acetonitrile, toluene, methanol and chloroform.

3. The method according to claim 1, wherein the mass of said organic solvent used is 1-200 times the mass of the raw materials.

4. The method according to claim 1, wherein the molar ratio of said aldehyde compound to said monoalkyl malonate is 1:1-5.

5. The method according to claim 1, wherein said metal compound in said catalyst is selected from the group consisting of one or a combination of copper triflate, copper sulfate, copper acetate, palladium acetate, ferrous fluoride, silver acetate, nickel acetate tetrahydrate, nickel acetylacetonate, nickel fluoride, nickel chloride hexahydrate, nickel sulfate, nickel perchlorate, and bistriphenylphosphine nickel chloride.

6. The method according to claim 1, wherein said chiral ligand in said catalyst is selected from one or a combination of the following: ##STR00042## ##STR00043##

7. The method according to claim 1, wherein the organic acid salt in said catalyst is selected from one or a combination of the following: ##STR00044## wherein the molar ratio of metal to salt in said catalyst is 1:1-3.

8. The method according to claim 1, wherein the ratio of said catalyst to said aldehyde compound is 1 wt %-20 wt %, and the molar ratio of the metal to the chiral ligand in said catalyst is 1:1-1.5.

9. The method according to claim 1, wherein said decarboxylation aldol addition reaction has a temperature of 0-60 C.

10. The method according to claim 2, wherein said decarboxylation aldol addition reaction has a reaction time of 3-120 hours.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the embodiments or the description of the prior art will be briefly described below. Obviously, the drawings in the following description are only certain embodiments of the present invention, and it is still within the scope of the present invention for those skilled in the art to obtain other drawings based on these drawings without any inventive labor.

(2) FIG. 1 is a structural diagram of a reaction product in an embodiment of the present invention.

DETAILED DESCRIPTIONS OF EMBODIMENTS

(3) In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be further described in detail with reference to the accompanying drawings.

Preferred Embodiment

(4) The method for chemically synthesizing the chiral -hydroxyl ester compound according to the present invention is specifically carried out according to the following steps: adding a metal catalyst and an organic acid salt to a reaction vessel under room temperature conditions, sufficiently dissolving with a solvent A, and stirring well 30-60 minutes, adding chiral ligand to the reaction vessel and stirring for 30-60 minutes, then adding common aldehyde and monoalkyl malonate, stirring at 20-30 C. to make the reaction 40-72 hours. In the hours, the progress of the reaction is monitored in real time, and after completion of the reaction, it is separated and purified, and after drying, the target compound of the chiral -hydroxy acid ester is obtained.

Example 1

(5) The ratio of the amount of the aldehyde having R.sup.1 as the para-nitrophenyl group, the monomethyl malonate having IV as the methyl group and the catalyst is 1.0:2.0:0.1. That is, the substrate p-nitrobenzaldehyde 302 mg (2 mmol), malonate monomethyl ester 472 mg (4 mmol), nickel acetate tetrahydrate 49.6 mg (0.2 mmol), chiral ligand L1 72.6 mg (0.22 mmol); the organic solvent is tetrahydrofuran 6.0 g, and the total amount is 20 times that of the substrate p-nitrobenzaldehyde.

(6) The metal catalyst and the chiral ligand L1 are added to the reaction vessel at room temperature, fully dissolved in tetrahydrofuran, stirred well for 30-60 minutes, and then p-nitrobenzaldehyde and monomethyl malonate are added to the reaction vessel. The mixture is stirred at 30 C. for 72 hours to complete the reaction.

(7) After the completion of the reaction, the mixture is separated and purified, and dried to give a white solid, which is 101.3 mg of the desired compound of the chiral -hydroxy acid ester, the yield is 45%, the enantioselective excess is 2% ee, and the purity is 99.0%. The structure of the desired compound is:

(8) Characterization data:

(9) ##STR00006##

(10) Daicel Chiralpak AS, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: tR (major)=17.1 min, tR (minor)=21.3 min. 1H NMR (500 MHz, CDCl3) 8.20 (d, J=8.7 Hz, 2H), 7.57 (d, J=8.6 Hz, 2H), 5.29-5.20 (m, 1H), 3.76 (d, J=5 Hz, 2H), 3.74 (s, 3H), 2.83-2.69 (in, 2H). 13C NMR (126 MHz, CDCl3) 172.27, 149.77, 147.29, 126.52, 123.76, 69.36, 52.10, 42.82.

Example 2

(11) The substrate p-nitrobenzaldehyde 302 mg (2 mmol), malonate monomethyl ester 472 mg (4 mmol), nickel acetate tetrahydrate 49.6 mg (0.2 mmol), chiral ligand L3 73.5 mg (0.22 mmol); the organic solvent is tetrahydrofuran 6.0 g, and the total amount is 20 times that of the substrate p-nitrobenzaldehyde.

(12) The metal catalyst and the chiral ligand L3 are added to the reaction vessel at room temperature, fully dissolved in tetrahydrofuran, stirred well for 30-60 minutes, and then p-nitrobenzaldehyde and monomethyl malonate are added to the reaction vessel. The mixture is stirred at 30 C. for 72 hours to complete the reaction.

(13) The rest processes are the same as those in Example 1, 60.1 mg of the target product 1a is obtained, the yield is 27%, the enantioselective excess is 9% ee, and the purity is 98.8%.

Example 3

(14) The substrate p-nitrobenzaldehyde 302 mg (2 mmol), malonate monomethyl ester 472 mg (4 mmol), nickel acetate tetrahydrate 49.6 mg (0.2 mmol), chiral ligand L5 (4) 86.5 mg (0.22 mmol); the organic solvent is tetrahydrofuran 6.0 g, and the total amount is 20 times that of the substrate p-nitrobenzaldehyde.

(15) The metal catalyst and the chiral ligand L5 are added to the reaction vessel at room temperature, fully dissolved in tetrahydrofuran, stirred well for 30-60 minutes, and then p-nitrobenzaldehyde and monomethyl malonate are added to the reaction vessel. The mixture is stirred at 30 C. for 72 hours to complete the reaction.

(16) The rest processes are the same as those in Example 1, 128.3 mg of the target product 1a is obtained, the yield is 57%, the enantioselective excess is 60% ee, and the purity is 99.8%.

Example 4

(17) The substrate p-nitrobenzaldehyde 302 mg (2 mmol), malonate monomethyl ester 472 mg (4 mmol), nickel acetate tetrahydrate 49.6 mg (0.2 mmol), chiral ligand L5 (4) 86.5 mg (0.22 mmol); the organic solvent is tetrahydrofuran 6.0 g, and the total amount is 20 times that of the substrate p-nitrobenzaldehyde.

(18) The metal catalyst and the chiral ligand L5 are added to the reaction vessel at room temperature, fully dissolved in tetrahydrofuran, stirred well for 30-60 minutes, and then p-nitrobenzaldehyde and monomethyl malonate are added to the reaction vessel. The mixture is stirred at 20 C. for 72 hours to complete the reaction.

(19) The rest processes are the same as those in Example 1, 83.3 mg of the target product 1a is obtained, the yield is 37%, the enantioselective excess is 77% ee, and the purity is 99.6%.

Example 5

(20) The substrate p-nitrobenzaldehyde 302 mg (2 mmol), malonate monomethyl ester 472 mg (4 mmol), nickel acetate 35.2 mg (0.2 mmol), chiral ligand L5 (4) 86.5 mg (0.22 mmol); the organic solvent is tetrahydrofuran 6.0 g, and the total amount is 20 times that of the substrate p-nitrobenzaldehyde.

(21) The metal catalyst and the chiral ligand L5 are added to the reaction vessel at room temperature, fully dissolved in tetrahydrofuran, stirred well for 30-60 minutes, and then p-nitrobenzaldehyde and monomethyl malonate are added to the reaction vessel. The mixture is stirred at 20 C. for 72 hours to complete the reaction.

(22) The rest processes are the same as those in Example 1, 105.8 mg of the target product 1a is obtained, the yield is 47%, the enantioselective excess is 77% ee, and the purity is 99.5%.

Example 6

(23) The substrate p-nitrobenzaldehyde 302 mg (2 mmol), malonate monomethyl ester 472 mg (4 mmol), nickel acetate 35.2 mg (0.2 mmol), o-nitrobenzoic acid sodium salt 75.6 mg (0.4 mmol), chiral ligand L5 (4) 86.5 mg (0.22 mmol); the organic solvent is tetrahydrofuran 6.0 g, and the total amount is 20 times that of the substrate p-nitrobenzaldehyde.

(24) At room temperature, the metal catalyst and o-nitrobenzoic acid sodium salt are added to the reaction vessel, and after fully dissolving with tetrahydrofuran, the mixture is stirred for 30-60 minutes, and then the chiral ligand L5 (4) is further stirred in the reaction vessel. After 30-60 minutes, a common aldehyde and a monoalkyl malonate are then added, and the mixture is stirred at 20 C. for 24 hours to complete the reaction.

(25) The rest processes are the same as those in Example 1, 119.3 mg of the target product 1a is obtained, the yield is 53%, the enantioselective excess is 80% ee, and the purity is 99.2%.

Example 7

(26) The substrate p-nitrobenzaldehyde 302 mg (2 mmol), malonate monomethyl ester 472 mg (4 mmol), nickel chloride hexahydrate 47.2 mg (0.2 mmol), o-nitrobenzoic acid sodium salt 75.6 mg (0.4 mmol), chiral ligand L5 (4) 86.5 mg (0.22 mmol); the organic solvent is tetrahydrofuran 6.0 g, and the total amount is 20 times that of the substrate p-nitrobenzaldehyde.

(27) The rest processes are the same as those in Example 1, 121.5 mg of the target product 1a is obtained, the yield is 54%, the enantioselective excess is 88% ee, and the purity is 99.7%.

Example 8

(28) The substrate p-nitrobenzaldehyde 302 mg (2 mmol), malonate monomethyl ester 472 mg (4 mmol), nickel chloride hexahydrate 47.2 mg (0.2 mmol), o-nitrobenzoic acid potassium salt 82 mg (0.4 mmol), chiral ligand L5 (4) 86.5 mg (0.22 mmol); the organic solvent is 6.0 g of tetrahydrofuran, and the total amount is 20 times that of the substrate p-nitrobenzaldehyde.

(29) The rest processes are the same as those in Example 6, 126 mg of the target product 1a is obtained, the yield is 56%, the enantioselective excess is 90% ee, and the purity is 99.3%.

Example 9

(30) The substrate p-nitrobenzaldehyde 302 mg (2 mmol), malonate monomethyl ester 472 mg (4 mmol), nickel chloride hexahydrate 47.2 mg (0.2 mmol), o-nitrobenzoic acid sodium salt 82 mg (0.4 mmol), chiral ligand L5 (4) 86.5 mg (0.22 mmol); the organic solvent is tetrahydrofuran 6.0 g, and the total amount is 20 times that of the substrate p-nitrobenzaldehyde.

(31) At room temperature, the metal catalyst and o-nitrobenzoic acid sodium salt are added to the reaction vessel, and after fully dissolving with tetrahydrofuran, the mixture is stirred for 30-60 minutes, and then the chiral ligand L5 (4) is further stirred in the reaction vessel. After 30-60 minutes, a common aldehyde and a monoalkyl malonate are then added, and the mixture is stirred at 15 C. for 60 hours to complete the reaction.

(32) The rest processes are the same as those in Example 1, 200.3 mg of the target product 1a is obtained, the yield is 89%, the enantioselective excess is 92% ee, and the purity is 99.6%.

Example 10-41, Corresponding Product 1b-1-Ag

(33) The substrate is an aldehyde (2 mmol) with different substituents, a monoalkyl malonate (4 mmol), nickel chloride hexahydrate 47.2 mg (0.2 mmol), o-nitrobenzoic acid sodium salt 82 mg (0.4 mmol), chiral ligand L5 (4) 86.5 mg (0.22 mmol); the organic solvent is tetrahydrofuran, and the total amount is 20 times that of the substrate p-nitrobenzaldehyde.

(34) At room temperature, the metal catalyst and o-nitrobenzoic acid sodium salt are added to the reaction vessel, and after fully dissolving with tetrahydrofuran, the mixture is stirred for 30-60 minutes, and then the chiral ligand L5 (4) is further stirred in the reaction vessel. After 30-60 minutes, a common aldehyde and a monoalkyl malonate are then added, and the mixture is stirred at 15 C. for 60 hours to complete the reaction.

(35) The rest processes are the same as in Example 1, and the target product 1 is obtained. The result is shown in FIG. 1:

(36) Specific characterization data for Examples 9-41 (1a-1ag):

Example 9

(37) ##STR00007##

Methyl 3-hydroxy-3-(4-nitrophenyl)propanoate (1a)

(38) 89% yield, []D.sup.25=+18.97 (c=0.26 in CHCl.sub.3), enantiomeric excess: 92%, Daicel Chiralpak AS, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=17.1 min, t.sub.R (minor)=21.3 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 8.20 (d, J=8.7 Hz, 2H), 7.57 (d, J=8.6 Hz, 2H), 5.29-5.20 (m, 1H), 3.76 (d, J=5 Hz, 2H), 3.74 (s, 3H), 2.83-2.69 (m, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.27, 149.77, 147.29, 126.52, 123.76, 69.36, 52.10, 42.82.

Example 10

(39) ##STR00008##

Ethyl 3-hydroxy-3-(4-nitrophenyl)propanoate (1b)

(40) 81% yield, []D.sup.25=+21.92 (c=0.26 in CHCl.sub.3), enantiomeric excess: 86%, Daicel Chiralpak AS, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=13.4 min, t.sub.R (major)=17.8 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 8.17 (d, J=8.7 Hz, 2H), 7.54 (d, J=8.6 Hz, 2H), 5.21 (dt, J=7.9, 3.8 Hz, 1H), 4.16 (q, J=7.1 Hz, 2H), 3.78 (d, J=3.6 Hz, 1H), 2.83-2.58 (m, 2H), 1.24 (t, J=7.1 Hz, 3H). .sup.13C NMR (126 MHz, CDCl.sub.3) 171.90, 149.82, 147.43, 126.52, 123.73, 69.38, 61.20, 42.98, 14.09.

Example 11

(41) ##STR00009##

Propyl 3-hydroxy-3-(4-nitrophenyl)propanoate (3c)

(42) 90% yield; [].sub.D.sup.25=17.88 (c=0.38 in CHCl.sub.3), enantiomeric excess: 84%, Daicel Chiralpak AS, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=10.4 min, t.sub.R (major)=14.3 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 8.17 (d, J=8.7 Hz, 2H), 7.54 (d, J=8.7 Hz, 2H), 5.21 (s, 1H), 4.06 (t, J=6.7 Hz, 2H), 3.79 (s, 1H), 2.83-2.57 (m, 2H), 1.67-1.47 (m, 2H), 0.90 (t, J=7.4 Hz, 3H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.00, 149.84, 147.41, 126.53, 123.72, 69.38, 66.78, 42.94, 21.84, 10.26.

Example 12

(43) ##STR00010##

Butyl 3-hydroxy-3-(4-nitrophenyl)propanoate (1d)

(44) 89% yield, [].sub.D.sup.25=17.77 (c=0.69 in CHCl.sub.3), enantiomeric excess: 84%, Daicel Chiralpak AS, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=8.8 min, t.sub.R (major)=10.6 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 8.18 (d, J=8.4 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 5.21 (dd, J=7.9, 3.8 Hz, 1H), 4.11 (t, J=6.7 Hz, 2H), 3.77 (d, J=3.6 Hz, 1H), 2.78-2.65 (m, 2H), 1.62-1.52 (m, 2H), 1.38-1.28 (m, 2H), 0.90 (t, J=7.4 Hz, 3H). .sup.13C NMR (126 MHz, CDCl.sub.3) 171.98, 149.81, 147.43, 126.52, 123.72, 69.39, 65.08, 42.95, 30.50, 19.03, 13.59.

Example 13

(45) ##STR00011##

(46) Isopropyl 3-hydroxy-3-(4-nitrophenyl)propanoate (1e): 87% yield, [].sub.D.sup.25=34.84 (c=0.26 in CHCl.sub.3), enantiomeric excess: 83%, Daicel Chiralpak AD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25: t.sub.R (major)=19.7 min, t.sub.R (minor)=22.1 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 8.19 (d, J=8.7 Hz, 2H), 7.55 (d, J=8.5 Hz, 2H), 5.24-5.17 (m, 1H), 5.05 (dt, J=12.5, 6.3 Hz, 1H), 3.78 (d, J=3.1 Hz, 1H), 2.78-2.60 (m, 2H), 1.23 (dd, J=7.7, 6.6 Hz, 6H). .sup.13C NMR (126 MHz, CDCl.sub.3) 171.50, 149.80, 147.15, 126.52, 123.73, 69.41, 68.95, 43.17, 21.74, 21.72.

Example 14

(47) ##STR00012##

Tert-butyl 3-hydroxy-3-(4-nitrophenyl)propanoate (1f)

(48) 75% yield, [].sub.D.sup.25=49.62 0.13 in CHCl.sub.3), enantiomeric excess: 80%, Daicel Chiralpak AD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=20.2 min, t.sub.R (minor)=22.5 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 8.20 (d, J=8.7 Hz, 2H), 7.55 (d, J=8.7 Hz, 2H), 5.17 (d, J=7.8 Hz, 1H), 3.85 (s, 1H), 2.65 (qd, J=16.6, 6.3 Hz, 2H), 1.45 (s, 9H). .sup.13C NMR (126 MHz, CDCl.sub.3) 171.41, 149.89, 147.40, 126.52, 123.69, 82.20, 69.49, 43.81, 28.05.

Example 15

(49) ##STR00013##

Methyl 3-(4-fluorophenyl)-3-hydroxypropanoate (1g)

(50) 71% yield, [].sub.D.sup.25=20.41 (c=0.29 in CHCl.sub.3), enantiomeric excess: 91%, Daicel Chiralpak OD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=11.1 min, t.sub.R (minor)=14.5 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.33 (dd, J=8.0, 5.6 Hz, 2H), 7.02 (t, J=8.6 Hz, 2H), 5.10 (t, 1H), 3.70 (s, 3H), 3.39 (d, J=2.6 Hz, 1H), 2.70 (qd, J=16.3, 6.4 Hz, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.58, 163.30, 161.34, 138.33, 127.39, 127.33, 115.45, 115.28, 69.68, 51.85, 43.19.

Example 16

(51) ##STR00014##

Methyl 3-(3-fluorophenyl)-3-hydroxypropanoate (1h)

(52) 74% yield, [].sub.D.sup.25=41.61 (c=0.26 in CHCl.sub.3), enantiomeric excess: 92%, Daicel Chiralpak OD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=11.2 min, t.sub.R (minor)=26.8 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.19 (dd, J=13.9, 7.1 Hz, 1H), 7.00 (t, J=8.2 Hz, 2H), 6.86 (td, J=8.5, 2.3 Hz, 1H), 5.06-4.94 (m, 1H), 3.70 (d, J=3.7 Hz, 1H), 3.59 (s, 3H), 2.65-2.54 (m, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.46, 163.91, 161.96, 145.45, 145.40, 130.07, 130.00, 121.23, 121.20, 114.61, 114.45, 112.76, 112.59, 69.64, 69.62, 51.87, 43.15.

Example 17

(53) ##STR00015##

Methyl 3-(2-fluorophenyl)-3-hydroxypropanoate (1i)

(54) 72% yield, [].sub.D.sup.25=62.79 (c=0.26 in CDCl.sub.3), enantiomeric excess: 90%, Daicel Chiralpak OD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=8.5 min, t.sub.R (minor)=24.3 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.42 (dd, J=10.8, 4.2 Hz, 1H), 7.15 (dt, J=13.4, 7.2 Hz, 1H), 7.04 (t, J=7.5 Hz, 1H), 6.94-6.85 (m, 1H), 5.35-5.24 (m, 1H), 3.72-3.63 (m, 1H), 3.59 (s, 3H), 2.64 (qd, J=16.3, 6.3 Hz, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.58, 160.41, 158.46, 129.72, 129.62, 129.14, 129.08, 127.25, 127.22, 124.35, 124.32, 115.28, 115.11, 64.52, 64.50, 51.83, 41.89.

Example 18

(55) ##STR00016##

Methyl 3-(4-chlorophenyl)-3-hydroxypropanoate (1j)

(56) 76% yield, [].sub.D.sup.25=44.17 (c=0.37 in CHCl.sub.3), enantiomeric excess: 90%, Daicel Chiralpak OB, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=15.0 min, t.sub.R (major)=16.7 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.41-7.22 (m, 4H), 5.24-4.93 (m, 1H), 3.71 (s, 3H), 3.52-3.46 (m, 1H), 2.79-2.61 (m, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.54, 141.07, 133.50, 128.69, 127.07, 69.62, 51.94, 43.08.

Example 19

(57) ##STR00017##

Methyl 3-(3-bromophenyl)-3-hydroxypropanoate (1k)

(58) 72% yield, [].sub.D.sup.25=46.40 (c=0.52 in CHCl.sub.3), enantiomeric excess: 94%, Daicel Chiralpak OD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=12.4 min, t.sub.R (minor)=41.2 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.53 (s, 1H), 7.40 (d, J=7.8 Hz, 1H), 7.27 (d, J=7.6 Hz, 1H), 7.21 (t, J=7.8 Hz, 1H), 5.13-5.05 (m, 1H), 3.71 (s, 3H), 3.58 (s, 1H), 2.75-2.64 (m, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.47, 144.92, 130.85, 130.12, 128.86, 124.28, 122.67, 69.59, 51.95, 43.08

Example 20

(59) ##STR00018##

Methyl 3-(2-bromophenyl)-3-hydroxypropanoate (1l)

(60) 71% yield, [].sub.D.sup.25=41.67 (c=0.25 in CHCl.sub.3), enantiomeric excess: 90%, Daicel Chiralpak OD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=14.0 min, t.sub.R (minor)=41.0 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.60 (dd, J=7.8, 1.2 Hz, 1H), 7.52-7.42 (m, 1H), 7.33 (t, J=7.4 Hz, 1H), 7.12 (td, J=7.8, 1.5 Hz, 1H), 5.43 (dd, J=9.8, 2.2 Hz, 1H), 3.72 (s, 3H), 3.68 (s, 1H), 2.85 (dd, J=16.5, 2.6 Hz, 1H), 2.55 (dd, J=16.5, 9.8 Hz, 1H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.71, 141.53, 132.65, 129.10, 127.84, 127.33, 121.40, 69.25, 51.95, 41.47.

Example 21

(61) ##STR00019##

Methyl 3-(4-cyanophenyl)-3-hydroxypropanoate (1m)

(62) 72% yield, [].sub.D.sup.25=44.73 (c=0.16 in CHCl.sub.3), enantiomeric excess: 85%, Daicel Chiralpak AD, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=15.3 min, t.sub.R (minor)=16.0 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.64 (d, J=8.1 Hz, 2H), 7.50 (d, J=8.1 Hz, 2H), 5.19 (t, J=6.4 Hz, 1H), 3.72 (s, 3H), 2.72 (d, J=6.4 Hz, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.24, 147.94, 132.36, 126.42, 118.65, 111.47, 69.51, 52.05, 42.89.

Example 22

(63) ##STR00020##

Methyl 3-(3-cyanophenyl)-3-hydroxypropanoate (1n)

(64) 72% yield, [].sub.D.sup.25=45.97 (c=0.34 in CHCl.sub.3), enantiomeric excess: 87%, Daicel Chiralpak AD, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=12.5 min, t.sub.R (major)=14.3 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.69 (s, 1H), 7.60 (d, J=7.8 Hz, 1H), 7.57 (d, J=7.7 Hz, 1H), 7.46 (t, J=7.7 Hz, 1H), 5.15 (d, J=1.6 Hz, 1H), 3.72 (s, 3H), 3.63 (d, J=2.7 Hz, 1H), 2.71 (d, J=6.4 Hz, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.34, 144.07, 131.40, 130.14, 129.41, 129.35, 118.64, 112.67, 69.24, 52.07, 42.87.

Example 23

(65) ##STR00021##

Methyl 3-(2-cyanophenyl)-3-hydroxypropanoate (10)

(66) 70% yield, [].sub.D.sup.25=50.67 (c=0.13 in CHCl.sub.3), enantiomeric excess: 73%, Daicel Chiralpak OD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=23.0 min, t.sub.R (major)=25.4 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.86 (d, J=7.5 Hz, 1H), 7.58 (t, J=7.5 Hz, 1H), 7.50 (t, J=7.4 Hz, 1H), 7.42 (d, J=7.6 Hz, 1H), 6.91 (s, 1H), 4.93 (dd, J=10.5, 3.0 Hz, 1H), 3.78 (s, 3H), 3.03 (dd, J=17.1, 3.4 Hz, 1H), 2.47 (dd, J=17.0, 10.6 Hz, 1H). .sup.13C NMR (126 MHz, CDCl.sub.3) 171.48, 170.47, 146.01, 132.00, 131.91, 128.58, 123.96, 122.38, 52.99, 52.15, 39.34.

Example 24

(67) ##STR00022##

Methyl 4-(1-hydroxy-3-methoxy-3-oxopropyl)benzoate (1p)

(68) 74% yield, [].sub.D.sup.25=32.39 (c=0.21 in CHCl.sub.3), enantiomeric excess: 91%, Daicel Chiralpak OD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=20.3 min, t.sub.R (major)=23.4 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.99 (d, J=8.1 Hz, 2H), 7.43 (d, J=8.4 Hz, 2H), 5.17 (s, 1H), 3.89 (s, 3H), 3.70 (s, 3H), 3.53 (s, 1H), 2.77-2.68 (m, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.02, 166.83, 147.60, 129.86, 129.60, 125.59, 69.87, 52.07, 51.93, 42.99.

Example 25

(69) ##STR00023##

Methyl 3-(1-hydroxy-3-methoxy-3-oxopropyl)benzoate (1q)

(70) 76% yield, [].sub.D.sup.25=55.47 (c=0.14 in CHCl.sub.3), enantiomeric excess: 90%, Daicel Chiralpak AD, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=14.9 min, t.sub.R (major)=18.5 min. .sup.1H NMR (500 MHz, CDCl3) 8.02 (s, 1H), 7.97-7.88 (m, 1H), 7.58 (d, J=7.5 Hz, 1H), 7.41 (t, J=7.7 Hz, 1H), 5.17 (dd, J=8.4, 4.3 Hz, 1H), 3.89 (d, J=0.7 Hz, 3H), 3.70 (s, 3H), 2.79-2.68 (m, 2H). .sup.13C NMR (126 MHz, CDCl3) 172.55, 166.90, 143.00, 130.44, 130.23, 128.99, 128.67, 126.85, 69.85, 52.13, 51.93, 43.07.

Example 26

(71) ##STR00024##

Methyl 3-(4-formylphenyl)-3-hydroxypropanoate (1r)

(72) 79% yield, [].sub.D.sup.25=32.93 (c=0.50 in CHCl.sub.3), enantiomeric excess: 90%, Daicel Chiralpak OD, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=15.7 min, t.sub.R (minor)=19.7 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 9.93 (s, 1H), 7.81 (d, J=8.2 Hz, 2H), 7.51 (d, J=8.1 Hz, 2H), 5.17 (s, 1H), 3.78-3.73 (m, 1H), 3.67 (s, 3H), 2.73-2.67 (m, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 191.91, 172.30, 149.46, 135.87, 129.99, 126.26, 69.81, 51.96, 43.00.

Example 27

(73) ##STR00025##

Methyl 3-(3-formylphenyl)-3-hydroxypropanoate (1s)

(74) 85% yield, [].sub.D.sup.25=31.79 (c=0.26 in CHCl.sub.3), enantiomeric excess: 85%, Daicel Chiralpak AD, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=15.1 min, t.sub.R (major)=16.7 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 10.00 (s, 1H), 7.89 (s, 1H), 7.79 (d, J=7.6 Hz, 1H), 7.65 (d, J=7.7 Hz, 1H), 7.52 (t, J=7.6 Hz, 1H), 5.21 (t, J=7.8 Hz, 1H), 3.72 (s, 3H), 3.58 (d, J=3.5 Hz, 1H), 2.80-2.71 (m, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 192.10, 172.50, 143.74, 136.43, 131.74, 129.28, 129.14, 126.84, 69.64, 51.98, 42.97.

Example 28

(75) ##STR00026##

Methyl 3-hydroxy-3-(2-methoxyphenyl)propanoate (1t)

(76) 70% yield, [].sub.D.sup.25=43.00 (c=0.13 CHCl.sub.3), enantiomeric excess: 85%, Daicel Chiralpak AD, hexane/iso-propanol=98/2, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=28.4 min, t.sub.R (major)=30.4 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.42 (d, J=7.5 Hz, 1H), 7.27-7.22 (m, 1H), 6.97 (t, J=7.4 Hz, 1H), 6.86 (d, J=8.2 Hz, 1H), 5.39-5.31 (m, 1H), 3.84 (s, 3H), 3.71 (s, 3H), 3.48 (d, J=4.2 Hz, 1H), 2.82 (dd, J=16.1, 3.4 Hz, 1H), 2.71 (dd, J=16.1, 9.3 Hz, 1H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.96, 156.04, 130.58, 128.60, 126.54, 120.82, 110.36, 66.55, 55.25, 51.71, 41.61.

Example 29

(77) ##STR00027##

Methyl 3-hydroxy-3-(3-methoxyphenyl)propanoate (1u)

(78) 71% yield, [].sub.D.sup.25=16.46 (c=0.24 in CHCl.sub.3), enantiomeric excess: 91%, Daicel Chiralpak AD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=19.2 min, t.sub.R (major)=21.9 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.26 (dd, J=10.2, 5.5 Hz, 1H), 6.93 (d, J=8.5 Hz, 2H), 6.82 (dd, J=8.1, 1.8 Hz, 1H), 5.10 (dd, J=9.0, 3.7 Hz, 1H), 3.80 (s, 3H), 3.71 (s, 3H), 3.36 (br, 1H), 2.72 (qd, J=16.3, 6.4 Hz, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.70, 159.84, 144.29, 129.59, 117.90, 113.39, 111.17, 70.25, 55.22, 51.86, 43.22.

Example 30

(79) ##STR00028##

Methyl 3-([1,1-biphenyl]-4-yl)-3-hydroxypropanoate (1v)

(80) 72% yield, [].sub.D.sup.25=9.35 (c=0.36 in CHCl.sub.3), enantiomeric excess: 90%, Daicel Chiralpak AD, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=12.6 min, t.sub.R (minor)=13.6 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.62-7.56 (m, 4H), 7.48-7.41 (m, 4H), 7.35 (t, J=7.3 Hz, 1H), 5.24-5.17 (m, 1H), 3.75 (s, 3H), 3.26 (d, J=3.4 Hz, 1H), 2.80 (qd, J=16.4, 6.4 Hz, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.75, 141.51, 140.84, 140.75, 128.78, 127.35, 127.33, 127.09, 126.12, 51.90, 43.10.

Example 31

(81) ##STR00029##

Methyl 3-(2-ethynylphenyl)-3-hydroxypropanoate (1w)

(82) 75% yield, [].sub.D.sup.25=45.20 (c=0.24 in CHCl.sub.3), enantiomeric excess: 82%, Daicel Chiralpak AD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=14.7 min, t.sub.R (major)=16.5 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.60 (d, J=7.8 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.40 (t, J=7.6 Hz, 1H), 7.25 (t, 1H), 5.57 (d, J=9.7 Hz, 1H), 3.74 (s, 3H), 3.48 (d, J=3.1 Hz, 1H), 3.36 (s, 1H), 2.90 (dd, J=16.5, 2.7 Hz, 1H), 2.66 (dd, J=16.5, 9.8 Hz, 1H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.91, 144.85, 132.89, 129.38, 127.25, 125.29, 119.19, 82.79, 81.00, 68.26, 51.88, 41.95.

Example 32

(83) ##STR00030##

methyl-3-hydroxy-3-(7-methoxybenzo[d][1,3]dioxol-5-yl)propanoate (1x)

(84) 71% yield, [].sub.D.sup.25=38.30 (c=0.20 in CHCl.sub.3), enantiomeric excess: 90%, Daicel Chiralpak AD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=35.6 min, t.sub.R (major)=44.6 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 6.57 (d, J=14.2 Hz, 2H), 5.96 (s, 2H), 5.04 (d, J=6.3 Hz, 1H), 3.90 (s, 3H), 3.73 (s, 3H), 3.20 (s, 1H), 2.70 (qd, J=16.3, 6.4 Hz, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.66, 149.00, 143.67, 137.32, 134.75, 105.30, 101.49, 99.93, 70.32, 56.63, 51.89, 43.31.

Example 33

(85) ##STR00031##

Methyl 3-hydroxy-3-(naphthalen-2-yl)propanoate (1y)

(86) 81% yield, [].sub.D.sup.25=13.56 (c=0.23 in CHCl.sub.3), enantiomeric excess: 91%, Daicel Chiralpak AD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=23.6 min, t.sub.R (major)=25.8 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.87-7.79 (m, 4H), 7.52-7.42 (m, 3H), 5.35-5.24 (m, 1H), 3.72 (d, J=7.5 Hz, 3H), 3.45 (d, J=2.9 Hz, 1H), 2.83 (qd, J=16.4, 6.4 Hz, 2H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.77, 139.88, 133.31, 133.06, 128.43, 128.03, 127.69, 126.25, 126.02, 124.47, 123.69, 70.46 (s), 51.92, 43.14.

Example 34

(87) ##STR00032##

Methyl 3-hydroxy-3-(naphthalen-1-yl)propanoate (1z)

(88) 82% yield, [].sub.D.sup.25=53.54 (c=0.13 in CHCl.sub.3), enantiomeric excess: 86%, Daicel Chiralpak OD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=27.6 min, t.sub.R (minor)=40.2 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 8.06 (d, J=8.3 Hz, 1H), 7.89 (d, J=7.9 Hz, 1H), 7.80 (d, J=8.2 Hz, 1H), 7.71 (d, J=7.1 Hz, 1H), 7.58-7.41 (m, 3H), 5.94 (d, J=9.6 Hz, 1H), 3.78 (s, 3H), 3.34 (d, J=3.1 Hz, 1H), 2.94 (dd, J=16.6, 2.9 Hz, 1H), 2.86 (dd, J=16.6, 9.7 Hz, 1H). .sup.13C NMR (126 MHz, CDCl.sub.3) 173.06, 137.97, 133.80, 129.97, 129.04, 128.35, 126.32, 125.64, 125.52, 122.95, 122.75, 67.37, 51.99, 42.56.

Example 35

(89) ##STR00033##

Methyl 3-(anthracen-9-yl)-3-hydroxypropanoate (1aa)

(90) 78% yield, [].sub.D.sup.25=21.63 (c=0.26 in CHCl.sub.3), enantiomeric excess: 76%, Daicel Chiralpak AD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=27.5 min, t.sub.R (major)=30.7 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 8.66 (s, 2H), 8.42 (s, 1H), 8.00 (d, J=8.3 Hz, 2H), 7.49 (dt, J=14.7, 6.9 Hz, 4H), 6.77 (dt, J=10.5, 2.7 Hz, 1H), 3.79 (s, 3H), 3.57 (dd, J=16.8, 10.7 Hz, 1H), 3.32 (d, J=2.8 Hz, 1H), 2.85 (dd, J=16.8, 3.1 Hz, 1H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.97, 132.28, 131.68, 129.38, 129.19, 128.57, 125.94, 124.85, 124.60, 77.29, 77.04, 76.78, 67.32, 52.00, 41.59.

Example 36

(91) ##STR00034##

Methyl (E)-3-hydroxy-5-(4-nitrophenyl)pent-4-enoate (lab)

(92) 79% yield, [].sub.D.sup.25=18.12 (c=0.26 in CHCl.sub.3), enantiomeric excess: 81%, Daicel Chiralpak OB, hexane/iso-propanol=85/15, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=33.8 min, t.sub.R (major)=35.0 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 8.18 (d, J=8.6 Hz, 2H), 7.51 (d, J=8.6 Hz, 2H), 6.77 (d, J=15.9 Hz, 1H), 6.41 (dd, J=15.9, 5.4 Hz, 1H), 4.78 (s, 1H), 3.75 (s, 3H), 3.23 (s, 1H), 2.72 (dd, J=16.5, 3.8 Hz, 1H), 2.64 (dd, J=16.5, 8.5 Hz, 1H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.42, 147.15, 142.96, 134.70, 128.55, 127.08, 124.00, 77.25, 77.00, 76.75, 68.26, 51.98, 40.94.

Example 37

(93) ##STR00035##

Methyl 3-hydroxy-4-oxo-4-phenylbutanoate (1ac)

(94) 71% yield, [].sub.D.sup.25=+15.01 (c=0.12 in MeOH), enantiomeric excess: 90%, Daicel Chiralpak AS, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=9.9 min, t.sub.R (minor)=12.0 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.92 (d, J=7.5 Hz, 2H), 7.59 (t, J=7.4 Hz, 1H), 7.48 (t, J=7.7 Hz, 2H), 5.41 (d, J=5.0 Hz, 1H), 4.04 (s, 1H), 3.67 (s, 3H), 2.86 (dd, J=15.9, 3.4 Hz, 1H), 2.60 (dd, J=15.9, 8.0 Hz, 1H). .sup.13C NMR (126 MHz, CDCl.sub.3) 199.85, 170.90, 134.05, 133.42, 128.95, 128.64, 70.22, 52.06, 40.17.

Example 38

(95) ##STR00036##

(96) (1ad): 76% yield, [].sub.D.sup.25=13.32 (c=0.51 in CHCl.sub.3), enantiomeric excess: 84%, Daicel AS, hexane/iso-propanol=90/10, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=11.1 min, t.sub.R (minor)=15.7 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 4.85 (d, J=5.7 Hz, 1H), 4.27-4.12 (m, 9H), 3.73 (s, 3H), 2.79-2.70 (m, 2H), 2.66 (s, 1H). .sup.13C NMR (126 MHz, CDCl.sub.3) 172.39, 91.60, 68.56, 68.17, 68.11, 66.56, 66.47, 66.04, 51.81, 42.65, 29.71.

Example 39

(97) ##STR00037##

Methyl 3-hydroxy-3-(thiophen-2-yl)propanoate (1ae)

(98) 76% yield, [].sub.D.sup.25=13.56 (c=0.15 in CHCl.sub.3), enantiomeric excess: 94%, Daicel Chiralpak OD, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=7.8 min, t.sub.R (major)=15.6 min. .sup.1H NMR (500 MHz, MeOD) 7.30 (d, J=4.5 Hz, 1H), 6.99 (d, J=3.2 Hz, 1H), 6.94 (dd, J=4.8, 3.7 Hz, 1H), 5.33 (dd, J=7.6, 6.1 Hz, 1H), 3.67 (s, 3H), 2.83-2.78 (m, 2H). .sup.13C NMR (126 MHz, MeOD) 172.89, 149.00, 127.61, 125.56, 124.68, 67.55, 52.22, 45.23.

Example 40

(99) ##STR00038##

Methyl 3-hydroxy-4-oxopentanoate (1af)

(100) 70% yield [].sub.D.sup.25=11.01 (c=0.10 in hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (major)=13.9 min, t.sub.R (minor)=18.7 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 4.38 (d, J=5.5 Hz, 1H), 3.77 (d, J=4.8 Hz, 1H), 3.71 (s, 3H), 2.88 (dd, J=16.4, 4.2 Hz, 1H), 2.75 (dd, J=16.4, 6.3 Hz, 1H), 2.28 (s, 3H). .sup.13C NMR (126 MHz, CDCl.sub.3) 208.11, 171.23, 73.75, 52.10, 37.92, 25.26

Example 41

(101) ##STR00039##

Methyl 3-hydroxy-5-phenylpentanoate (1ag)

(102) 72% yield, [].sub.D.sup.25=+18.97 (c=0.26 in CHCl.sub.3), enantiomeric excess: 77%, Daicel Chiralpak OB, hexane/iso-propanol=95/5, flow rate 1.0 mL/min, 25 C.: t.sub.R (minor)=15.5 min, t.sub.R (major)=16.9 min. .sup.1H NMR (500 MHz, CDCl.sub.3) 7.26-7.03 (m, 5H), 4.08-3.84 (m, 1H), 3.63 (s, 3H), 2.79-2.70 (m, 1H), 2.66-2.59 (m, 1H), 2.41 (qd, J=16.5, 6.0 Hz, 2H), 1.82-1.71 (m, 1H), 1.71-1.63 (m, 1H). .sup.13C NMR (126 MHz, CDCl.sub.3) 173.33, 141.70, 128.45, 128.43, 125.91, 67.25, 51.73, 41.16, 38.12, 31.76.

(103) The above is only the preferred embodiment of the present invention, and the scope of the present invention is not limited thereto, and thus equivalent changes made in the claims of the present invention are still within the scope of the present invention.