从氨基酸合成1,3,4-三取代4-羧基β-内酰胺衍生物时的卓越立体选择性。

Exceptional stereoselectivity in the synthesis of 1,3,4-trisubstituted 4-carboxy beta-lactam derivatives from amino acids.

作者信息

Pérez-Faginas Paula, O'Reilly Fran, O'Byrne Aisling, García-Aparicio Carlos, Martín-Martínez Mercedes, Pérez de Vega M Jesús, García-López M Teresa, Gonzalez-Muñiz Rosario

机构信息

Instituto de Química Médica (CSIC), Juan de la Cierva, 3, 28006 Madrid, Spain.

出版信息

Org Lett. 2007 Apr 12;9(8):1593-6. doi: 10.1021/ol070533d. Epub 2007 Mar 24.

DOI:10.1021/ol070533d

PMID:17381101

Abstract

[reaction: see text] The base-promoted cyclization of optically pure N-(p-methoxybenzyl)-N-(2-chloro)propionyl amino acid derivatives resulted in a diastereo- and enantioselective approach to valuable 1,3,4,4-tetrasubstituted beta-lactams. The stereochemical outcome of the reaction is exclusively governed by the configuration of the N-(2-chloro)propionyl moiety.

摘要

[反应：见正文] 光学纯的N-（对甲氧基苄基）-N-（2-氯）丙酰基氨基酸衍生物在碱促进下的环化反应，为合成有价值的1,3,4,4-四取代β-内酰胺提供了一种非对映和对映选择性方法。该反应的立体化学结果完全由N-（2-氯）丙酰基部分的构型决定。