OPTICALLY ACTIVE CARBOXYLIC ACID AND ITS PRODUCTION

• Main Authors: YAMAMOTO YOSHIHIRO, SHIMAZAKI TOSHIYUKI, AWANO HIROICHI, OKUMURA KUNIO, YAMASHITA HIROYUKI
• Format: Patent
• Language: English
• Published: 02.09.1997
• Edition: 6
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; APPARATUS THEREFOR; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; GENERAL METHODS OF ORGANIC CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; THEIR RELEVANT APPARATUS; TRANSPORTING

PROBLEM TO BE SOLVED: To obtain the subject compound useful as an intermediate for pharmaceuticals in high optical yield by the asymmetric hydrogenation reaction using a transition metal-optically active phosphine complex. SOLUTION: An optically active carboxylic acid of formula II is produced by the asymmetric hydrogenation of (A) a β,γ-unsaturated carboxylic acid of formula I (R is H, amino, acetylamino, t-butoxycarbonylamino or p- cyanobenzoylamino; X is O or CH2 ) using (B) a transition metal-optically active phosphine complex as a catalyst. The transition metal is preferably ruthenium, rhodium or iridium, especially ruthenium. The optically active phosphine in the component B is preferably a binaphthyl compound of formula III (R is phenyl or cyclohexyl which may have methyl, t-butyl or methoxy substituent; X is H, amino, acetylamino, etc.).