(2S,5R)-5-羟基哌啶酸及其6-取代衍生物的非对映选择性合成

Diastereoselective synthesis of (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives.

作者信息

Botman Peter N M, Dommerholt F Jan, de Gelder René, Broxterman Quirinus B, Schoemaker Hans E, Rutjes Floris P J T, Blaauw Richard H

机构信息

Chiralix B.V., P.O. Box 31070, 6503 CB Nijmegen, The Netherlands.

出版信息

Org Lett. 2004 Dec 23;6(26):4941-4. doi: 10.1021/ol047774v.

DOI:10.1021/ol047774v

PMID:15606105

Abstract

[reaction: see text] Herein, we report a diastereoselective synthesis of the natural product (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives thereof. The key step in the synthetic sequence is a novel highly diastereoselective epoxidation reaction of an enantiomerically pure cyclic enamide intermediate.

摘要

[反应：见正文] 在此，我们报道了天然产物(2S,5R)-5-羟基哌啶酸及其6-取代衍生物的非对映选择性合成。合成序列中的关键步骤是对映体纯的环状烯酰胺中间体的一种新型高度非对映选择性环氧化反应。