The invention comprises novel chiral metal complex compounds of the formula ##STR00001## wherein M, PR.sup.2, R.sup.3 and R.sup.4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.

The invention comprises novel chiral metal complex compounds of the formula ##STR00001## wherein M, PR.sup.2, R.sup.3 and R.sup.4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.

The invention comprises novel chiral metal complex compounds of the formula

##STR00001##

wherein M, PR.sup.2, R.sup.3 and R.sup.4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.

The invention comprises novel chiral metal complex compounds of the formula

##STR00001##

wherein M, PR.sup.2, R.sup.3 and R.sup.4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.

There is described a method of preparing a compound of formula I, and optical isomers thereof; in which R.sup.1 is hydrogen or a protecting group; said method comprising oxidizing verbenone and optical isomers thereof. ##STR00001##

There is described a method of preparing a compound of formula I, and optical isomers thereof; in which R.sup.1 is hydrogen or a protecting group; said method comprising oxidizing verbenone and optical isomers thereof. ##STR00001##

There is described a method of preparing a compound of formula I, and optical isomers thereof; in which R.sup.1 is hydrogen or a protecting group; said method comprising oxidizing verbenone and optical isomers thereof. ##STR00001##

An inexpensive, stereoselective synthesis for nootkatone, tetrahydronootkatone, and their derivatives is disclosed utilizing ozonolysis. The starting materials used in the synthesis are inexpensive and the reactions are commercially feasible and amenable to scaling up. The principal starting material, ()--Pinene, is on the GRAS list (generally recognized as safe).

An inexpensive, stereoselective synthesis for nootkatone, tetrahydronootkatone, and their derivatives is disclosed utilizing ozonolysis. The starting materials used in the synthesis are inexpensive and the reactions are commercially feasible and amenable to scaling up. The principal starting material, ()--Pinene, is on the GRAS list (generally recognized as safe).

The invention relates to the use of the compounds of formula (I) as an odoriferous substance.

##STR00001##