The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol
The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol
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DOI：
10.1016/s0040-4020(96)01169-6
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发表时间：
1997-02-10
期刊：
影响因子：
2.1
通讯作者：
Evans, JC
中科院分区：
文献类型：
--
作者：
Curran, TT;Hay, DA;Evans, JC
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.
