Hamari Chemicals, Ltd.

Sadayuki Maeda

Tatsunori Sato

Toshio Miyawaki

Yasuhiko Kawano

Masahiro Takaya

Naomichi Mitsumori

Usao Nakamura

Iwao Shimizu

Susumu Arashida

Shinji Takenaka

Yasutaka Shinoo

Yoshifumi Maki

Makoto Sakanaka

Magoichi Sako

A method is provided for producing optically active alcohols from ketones by reducing a ketone in the presence of an iridium(III) complex having a chiral prolinamide compound as a ligand. The ketone is preferably a compound represented by formula [I]: 

Method for producing optically active alcohols

Provided are a novel chiral iridium(III) complex; and a method for producing optically active 2-substituted-1,2,3,4-tetrahydroquinolines from 2-substituted-quinolines with the use of the chiral iridium(III) complex through a more economical and easy production process. The disclosed method for producing optically active 2-substituted-1,2,3,4-tetrahydroquinolines comprises reducing a quinoline compound represented by formula [I]: in the presence of a hydrogen donor compound and an iridium (III) complex having a chiral prolinamide compound as a ligand to give an optically active 2-substituted-1,2,3,4-tetrahydroquinoline represented by formula [II]: 

Method for producing optically active tetrahydroquinolines

The present invention provides a method for producing chiral amines, comprising asymmetric transfer hydrogenation of imine compounds in the presence of a hydrogen donor compound and an iridium(III) complex having a chiral prolinamide compound as a ligand. The present invention is useful for production of chiral amines in an efficient manner in terms of their optical and chemical yields.

Method for producing optically active amines

N.sup..epsilon. -Trifluoroacetyl-L-lysyl-L-proline.D-10-camphorsulfonic acid salt is produced in very high purity by reacting N.sup..epsilon. -trifluoroacetyl-L-lysyl-L-proline with D-10-camphorsulfonic acid in a suitable solvent, followed by crystallization from the reaction mixture. The salt is extremely stable at a temperature of working ambience as compared with other salts of N.sup..epsilon. -trifluoroacetyl-L-lysyl-L-proline including known dicyclohexylamine salt of the same.

N.sup..epsilon. -trifluoroacetyl-L-lysyl-L-proline.D-10-camphorsulfonic

A 2-(substituted aryl)propionaldehyde of the formula, ##STR1## (wherein Ar denotes ##STR2## is produced in high yield by reacting a methyl (substituted aryl) ketone of the formula ##STR3## with phenyldimethylsulfonium methylsulfate of the formula, ##STR4## in the presence of alkali metal hydroxide to obtain a reaction mixture containing 2-(substituted aryl)1,2-epoxypropane of the formula, ##STR5## and thioanisole, and subjecting the reaction mixture to contact with anhydrous MgCl.sub.2. The propionaldehyde compound is also produced in high yield by contacting the epoxypropane compound with anhydrous MgCl.sub.2 in the presence of a soft nucleophile such as a sulfide, a thiol and a phosphine.

Method for producing 2-(substituted aryl) propionaldehyde

Novel 1,5-benzothiazepine derivatives having the formula; ##STR1## (wherein R.sub.1, R.sub.2 and R.sub.3 each denotes hydrogen, a halogen, a lower alkyl group, a lower alkoxy group or a hydroxy group; R.sub.4 denotes a lower alkyl group, an allyl group, a lower alkoxyalkyl group, a lower alkyl group substituted with a hydroxy group or a halogen, a lower alkylaminoalkyl group or a morpholino lower alkyl group; X denotes a halogen or hydrogen) are produced from corresponding 1,4-benzothiazine by a ring expansion reaction with trimethylhalosilane, hydrogen peroxide and water. The derivatives have analgesic, antipyretic and antiarrythmic activities.

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Kyoto, Japan

Sadayuki Maeda