Tertiary amino-alcohol compound and production of optically active secondary alcohol using said compound

Abstract

Abstract PURPOSE: To obtain an optically active secondary alcohol in high yield and in high optical purity, by subjecting a dialkylzinc to asymmetric addition reaction to an aldehyde by using a specific tertiary amino-alcohol as a catalyst. CONSTITUTION: A dialkylzinc is added to an aldehyde by using a compound shown by formula I [R 4 is 1W6C alkyl; R 5 and R 6 are H or phenyl which may contain 1W5 substituent groups (halogen or NO 2 ); Z is H, Li, Na, K or MgC 2 H 5 ; *is optically active carbon] such as (S)-diphenyl(1-methylpyrrolidin-2-yl) methanol as a catalyst to give an optically active secondary alcohol shown by formula II [R 1 is 1W12C alkyl; R 2 is 1W12C alkyl or group shown by formula III (X and Y are Y, halogen, NO 2 or CN; m and n are 0W2; α and β are single bond, COO, OOC, OCH 2 , OCH 2 O or O; R 3 is 1W16C alkyl)]. The amount of the catalyst used is ≤5mol.% based on the aldehyde and that of the dialkylzinc is 1W2.5 equivalents. COPYRIGHT: (C)1989,JPO&Japio

Inventors

• 👤 Kenzou Kougou

Bibliographic Details