Synthesis of New Chiral Building Blocks via an Enzymatic Reaction: A New Method of Enhancing Enantioselectivity of the Enzymatic Reaction

Abstract

This review describes efficient means of preparing optically pure compounds via bakers' yeast mediated reaction or lipase-catalyzed reaction: (1) Bakers' yeast mediated reaction of cyanoketone was demonstrated and was discovered a new type of C-C bond forming reaction. (2) Hydrolysis of 2-substituted-3-acetoxy esters by Aspergillus lipase (lipase A 6) was demonstrated. According to summarize the stereo favoritismbetween substrates, the active site model of an Aspergillus lipase is proposed. (3) A simple preparation of optically active α- or γ-hydroxystannanes using Pseudomonas lipase (lipase PS) was realized. (4) Two effective means were discovered for enantioselective reaction of lipase PS: one is the modification of the acyl group by a sulfur functional group and the other is addition of a catalytic amount of l-methioninol or crown ether derivatives to the reaction mixture. (5) Optically pure (R) -4-hydroxy-3- (3,4-methylenedioxyphenyl) methylbutanenitrile, obtained by this reaction, was applied to the synthesis of three anti-tumor lignans. (6) As a new chiral building block for tertiary alcohols, (R) -2-ally1-2-(phenylthio) methyloxirane was synthesized via lipase-catalyzed reaction. © 1994, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.