Tetrahedron Letters

Novel aziridination of α-halo ketones: an efficient nucleophile-induced cyclization of phosphoramidates to functionalized aziridines

LDS Yadav, A Rai, VK Rai, C Awasthi

Index: Yadav, Lal Dhar S.; Rai, Ankita; Rai, Vijai K.; Awasthi, Chhama Tetrahedron Letters, 2008 , vol. 49, # 4 p. 687 - 690

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Citation Number: 24

Abstract

A novel and efficient aziridination of α-halo ketones is reported. The reaction of α-halo ketones with diethyl N-arylphosphoramidates affords diethyl N-aryl-N-(2-oxoalkyl) phosphoramidates which undergo reductive (H−-induced) cyclization with sodium borohydride followed by sodium hydride to give 1, 2-disubstituted and 1, 2, 3-trisubstituted aziridines. The cyclization induced by NCS− or PhS− affords substituted aziridines ...