The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol

被引：73

作者：

Curran, TT

Hay, DA

Koegel, CP

Evans, JC

机构：

[1] HOECHST MARION ROUSSEL INC, CINCINNATI, OH 45215 USA

[2] DOW CHEM CO USA, MIDLAND, MI 48674 USA

来源：

TETRAHEDRON | 1997年 / 53卷 / 06期

关键词：

D O I：

10.1016/S0040-4020(96)01169-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation and enzymatic resolution of several cis-mono-4-O-protected-2-cyclopenten-1,4-diols are described. The process starts with inexpensive furfuryl alcohol and lends itself to the preparation of multigram quantities of various protected, optically active 2-cyclopenten-1,4-diol derivatives. Stereoselective reduction of 4-O-protected-2-cyclopentenone to the cis-mono-O-protected-2-cyclopenten-1,4-diol using LiAlH4/LiI or Red-Al(R)/NaI is described. Subsequent pancreatin-promoted, stereoselective acylation was conducted on these cis-(+/-)-mono-O-protected-cyclopenten-1,4-diols to afford the corresponding alcohols and acetates in moderate to excellent enantioselectivities. (C) 1997, Elsevier Science Ltd.

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页码：1983 / 2004

页数：22

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