使用固相负载胺实现由氧化膦衍生的2H-氮杂环丙烷的不对称合成。氮杂环丙烷与羧酸的开环反应。

Asymmetric synthesis of 2H-azirines derived from phosphine oxides using solid-supported amines. Ring opening of azirines with carboxylic acids.

作者信息

Palacios Francisco, Aparicio Domitila, Ochoa De Retana Ana María, de los Santos Jesús M, Gil José Ignacio, Alonso José María

机构信息

Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain.

出版信息

J Org Chem. 2002 Oct 18;67(21):7283-8. doi: 10.1021/jo025995d.

DOI:10.1021/jo025995d

PMID:12375955

Abstract

A simple and efficient asymmetric synthesis of 2H-azirine-2-phosphine oxides 3 is described. The key step is a solid-phase bound achiral or chiral amine-mediated Neber reaction of beta-ketoxime tosylates derived from phosphine oxides 1. Reaction of 2H-azirines 3 and 11 with carboxylic acids 4 gives phosphorylated ketamides 5 and 12. Ring closure of ketamides 5 and 12 with triphenylphosphine and hexachloroethane in the presence of triethylamine leads to the formation of phosphorylated oxazoles 8 and 13.

摘要

本文描述了一种简单高效的2H-氮丙啶-2-氧化膦3的不对称合成方法。关键步骤是由氧化膦1衍生的β-酮肟对甲苯磺酸盐的固相键合非手性或手性胺介导的内伯反应。2H-氮丙啶3和11与羧酸4反应生成磷酸化酮酰胺5和12。在三乙胺存在下，酮酰胺5和12与三苯基膦和六氯乙烷闭环生成磷酸化恶唑8和13。