Provided is a process for producing an optically active hydroxyaldehyde or aminohydroxyaldehyde. The process for producing an optically active hydroxyaldehyde or aminohydroxyaldehyde is characterized by reacting an aldehyde or an imine with a boric acid enol ester in the presence of a copper compound and an optically active bidentate phosphine compound.

The present disclosure generally relates to the catalytic conversion of alcohols into hydrocarbon ketones suitable for use as fuels. More specifically, the present disclosure relates to the catalytic conversion of a mixture of isopropanol-butanol-ethanol (IBE) or acetone-butanol-ethanol (ABE), into ketones suitable for use as fuels. The ABE or IBE mixtures may be obtained from the fermentation of biomass or sugars.

The present disclosure generally relates to the catalytic conversion of alcohols into hydrocarbon ketones suitable for use as fuels. More specifically, the present disclosure relates to the catalytic conversion of a mixture of isopropanol-butanol-ethanol (IBE) or acetone-butanol-ethanol (ABE), into ketones suitable for use as fuels. The ABE or IBE mixtures may be obtained from the fermentation of biomass or sugars.

The present disclosure generally relates to the catalytic conversion of alcohols into hydrocarbon ketones suitable for use as fuels. More specifically, the present disclosure relates to the catalytic conversion of a mixture of isopropanol-butanol-ethanol (IBE) or acetone-butanol-ethanol (ABE), into ketones suitable for use as fuels. The ABE or IBE mixtures may be obtained from the fermentation of biomass or sugars.

Spiro-thiazolones of formula I

##STR00001## wherein X.sup.1, X.sup.2, X.sup.3, X.sup.4, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are as defined herein, which act as V1a receptor modulators, and in particular as V1a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use as medicaments for treatment of inappropriate secretion of vasopressin, anxiety, depressive disorders, obsessive compulsive disorder, autistic spectrum disorders, schizophrenia, aggressive behavior and phase shift sleep disorders, in particular jetlag.

Spiro-thiazolones of formula I

##STR00001## wherein X.sup.1, X.sup.2, X.sup.3, X.sup.4, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are as defined herein, which act as V1a receptor modulators, and in particular as V1a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use as medicaments for treatment of inappropriate secretion of vasopressin, anxiety, depressive disorders, obsessive compulsive disorder, autistic spectrum disorders, schizophrenia, aggressive behavior and phase shift sleep disorders, in particular jetlag.

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent expressed as a 3-methyl-3-butenyl M of General Formula (8):

##STR00001##

wherein M is a cationic moiety, with an acetal compound of General Formula (9):

##STR00002##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.

There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent expressed as a 3-methyl-3-butenyl M of General Formula (8):

##STR00001##

wherein M is a cationic moiety, with an acetal compound of General Formula (9):

##STR00002##

wherein R.sup.1 and R.sup.2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.

An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.

An object of the present invention is to enable the synthesis of various fluorine-containing compounds having an organic group at both terminals of their tetrafluoroethylene structure (—CF.sub.2—CF.sub.2—). The present invention provides a fluorine-containing complex compound including a fluorine-containing organic metal compound represented by formula (1a):
R.sup.1—CF.sub.2—CF.sub.2-M.sup.1  (1a)
wherein M.sup.1 is a metal selected from the group consisting of copper, zinc, nickel, iron, cobalt, and tin; and R.sup.1 represents an organic group, and at least one ligand selected from the group consisting of pyridine ring-containing compounds and phosphines.