手性 N-亚氨基-2-苯基-1,2-二氢吡啶中间体立体选择性合成 L-哌啶酸和(2S,3S)-3-羟基哌啶酸。

Stereoselective syntheses of L-pipecolic acid and (2S,3S)-3-hydroxypipecolic acid from a chiral N-imino-2-phenyl-1,2-dihydropyridine intermediate.

机构信息

Département de chimie, Universit de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada, H3C 3J7.

出版信息

J Org Chem. 2010 Mar 19;75(6):2077-80. doi: 10.1021/jo902527s.

PMID:20184299

Abstract

Stereoselective syntheses of L-pipecolic acid and (2S,3S)-3-hydroxypipecolic acid were achieved from a chiral N-imino-2-phenyl-1,2-dihydropyridine intermediate. The 3-hydroxy substituent of the latter amino acid was introduced by hetero-Diels-Alder reaction of singlet oxygen with the 1,2-dihydropyridine.

摘要

从手性 N-亚氨基-2-苯基-1,2-二氢吡啶中间体实现了 L-哌啶酸和（2S,3S）-3-羟基哌啶酸的立体选择性合成。后者氨基酸的 3-羟基取代基是通过单线态氧与 1,2-二氢吡啶的杂[4+2]环加成反应引入的。