- 著者
-
伊藤 敏幸
高木 由美子
- 出版者
- The Society of Synthetic Organic Chemistry, Japan
- 雑誌
- 有機合成化学協会誌 (ISSN:00379980)
- 巻号頁・発行日
- vol.52, no.1, pp.59-71, 1994-01-01 (Released:2009-11-16)
- 参考文献数
- 40
- 被引用文献数
-
2
3
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 favoritism between 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.