Asymmetric synthesis of 2H-aziridine phosphonates, and α-or β-aminophosphonates from enantiomerically enriched 2H-azirines

F Palacios, D Aparicio, AMO de Retana, M Jesús…

Index: Palacios, Francisco; Aparicio, Domitila; Ochoa de Retana, Ana Maria; De Los Santos, Jesus M.; Gil, Jose I.; Lopez de Munain, Rafael Tetrahedron Asymmetry, 2003 , vol. 14, # 6 p. 689 - 700

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Citation Number: 66

Abstract

A simple and efficient method for asymmetric synthesis of 2H-azirine-2-phosphonates 6 is described. The key step is a base-mediated Neber reaction of p-toluenesulfonyloximes 4 derived from phosphonates. Triethylamine 5, alkaloids 7 and solid-phase bound achiral 8 or chiral amines 9 are used. Reduction of 2H-azirines 6 with sodium borohydride in ethanol gives cis-aziridine-phosphonates 10. Ring opening of aziridines 10 and 11 leads to the ...