胺衍生物对共轭亚磷酰基和亚磷酰基亚硝基烯烃的迈克尔加成反应。α-氨基氧化膦和膦酸酯衍生物的制备。

Michael addition of amine derivatives to conjugate phosphinyl and phosphonyl nitrosoalkenes. Preparation of alpha-amino phosphine oxide and phosphonate derivatives.

作者信息

de los Santos Jesús M, Ignacio Roberto, Aparicio Domitila, Palacios Francisco

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. 2007 Jul 6;72(14):5202-6. doi: 10.1021/jo0705521. Epub 2007 Jun 19.

DOI:10.1021/jo0705521

PMID:17579451

Abstract

The synthesis of nitrosoalkenes derived from phosphine oxides and phosphonates generated through base-mediated dehydrohalogenations of readily available alpha-halooximes is reported. These highly reactive intermediates act as Michael acceptors toward nucleophilic reagents such as ammonia, amines, and optically active amino esters, furnishing alpha-amino phosphine oxides and phosphonates in a highly regioselective fashion.

摘要

据报道，通过碱介导的易得α-卤代肟的脱卤化氢反应生成的氧化膦和膦酸酯衍生的亚硝基烯烃得以合成。这些高活性中间体作为迈克尔受体，与亲核试剂如氨、胺和旋光性氨基酯发生反应，以高度区域选择性的方式生成α-氨基氧化膦和膦酸酯。