Synthesis of new α or γ-functionalized hydroxymethylphosphinic acid derivatives

被引：27

作者：

Cristau, HJ ^{[1
]}

Hervé, A ^{[1
]}

Virieux, D ^{[1
]}

机构：

[1] Ecole Natl Super Chim Montpellier, Chim Organ Lab, UMR 5076, Montpellier 5, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 04期

关键词：

phosphinic acid; Kabachnik-fields reaction; ester group;

D O I：

10.1016/j.tet.2003.11.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of new gamma-ethoxycarbonyl- and alpha-amino-alkyl hydroxymethylphosphinic acid derivatives are described. These compounds were conveniently prepared by Michael addition or Kabachnik-Fields reaction of an original precursor, ethyl benzyloxymethyl hydrogenophosphinate, respectively to alpha,beta-unsaturated esters using a basic activation or to imines. Selective deprotection of the alcohol function was achieved by hydrogenolysis on Pd/C, whereas lithium bromide was used to selectively cleave the phosphinate ester group. Acidic hydrolysis readily gave the free hydroxymethylphosphinic acids. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：877 / 884

页数：8

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