Enzymatic resolution of 5-phenylselanyltetrahydro-2-furanone.: Enantioselective preparation of (R) and (S)-γ-valerolactone

被引：14

作者：

Clososki, GC

Costa, CE

Missio, LJ

Cass, QB

Comasseto, JV

机构：

[1] Univ Sao Paulo, Inst Quim, BR-05599070 Sao Paulo, Brazil

[2] Univ Fed Sao Carlos, Dept Quim, Sao Carlos, SP, Brazil

来源：

SYNTHETIC COMMUNICATIONS | 2004年 / 34卷 / 05期

基金：

巴西圣保罗研究基金会;

关键词：

gamma-valerolactone; 5-phenylselenyltetrahydro-2-furanone; porcine pancreatic lipase;

D O I：

10.1081/SCC-120028354

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lipase-catalyzed lactonization of (2) provides both (R) and (S) enantiomers of 5-phenylselenyltetrahydro-2-furanone (1) in good enantiomeric excess. The kinetic resolution was examined using PPL (Porcine pancreatic lipase), PSL (Amano PS, Pseudomonas sp. lipase), MML (Mucor miehei lipase), CRL (Candida rugosa lipase), CAL-B (Candida Antarctica lipase, type B) and Novozym 435 (immobilized C. antarctica lipase type B) in different solvents. A tributyltin hydride reduction of enantiomerically enriched 1 gave both (R) and (S) enantiomers of S-4pentanolide (gamma-valerolactone).

引用

页码：817 / 828

页数：12

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