α-磷酸化α,β-不饱和亚胺的合成及其选择性还原为烯醇式和饱和α-氨基膦酸酯。

Synthesis of alpha-phosphorylated alpha,beta-unsaturated imines and their selective reduction to vinylogous and saturated alpha-aminophosphonates.

作者信息

Palacios Francisco, Vicario Javier, Maliszewska Agnieszka, Aparicio Domitila

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 Mar 30;72(7):2682-5. doi: 10.1021/jo062609+. Epub 2007 Mar 1.

DOI:10.1021/jo062609+

PMID:17328577

Abstract

An efficient synthesis of alpha,beta-unsaturated imines derived from alpha-aminophosphonates is achieved through aza-Wittig reaction of P-trimethyl phosphazenes with beta,gamma-unsaturated alpha-ketophosphonates. Selective 1,2-reduction of such 1-azadienes affords beta,gamma-unsaturated alpha-aminophosphonates, phosphorylated analogs of vinylglycines, which are hydrogenated to yield saturated alpha-aminophosphonate derivatives.

摘要

通过磷三甲基磷腈与β,γ-不饱和α-酮基膦酸酯的氮杂维蒂希反应，实现了由α-氨基膦酸酯衍生的α,β-不饱和亚胺的高效合成。对这类1-氮杂二烯进行选择性1,2-还原，可得到β,γ-不饱和α-氨基膦酸酯，即乙烯基甘氨酸的磷酸化类似物，将其氢化可生成饱和α-氨基膦酸酯衍生物。