Tetrahedron: Asymmetry

Diastereoselective synthesis of novel 5-substituted morpholine-3-phosphonic acids: further exploitation of N-acyliminium intermediates

I Bonilla-Landa, JL Viveros-Ceballos…

Index: Bonilla-Landa, Israel; Viveros-Ceballos, Jose Luis; Ordonez, Mario Tetrahedron Asymmetry, 2014 , vol. 25, # 6-7 p. 485 - 487

Full Text: HTML

Citation Number: 7

Abstract

Abstract The first diastereoselective total synthesis of 5-substituted morpholine-3- phosphonic acids is reported. The principal feature of the synthesis is the introduction of a dimethyl phosphonate group into 5-substituted morpholin-3-ones. The procedure is based on the preparation of N-Boc-(S)-5-phenyl-and N-Boc-(S)-5-benzylmorpholin-3-one from l- phenylglycine and l-phenylalanine methyl esters, followed by the formation of the 3- ...