Tetrahedron

A general method for the synthesis of O-alkyl N, O′-arylphosphoramidates and its application to the synthesis of a transition state analogue for carbamate hydrolysis

SD Taylor, MJ Chen, AN Dinaut, RA Batey

Index: Taylor, Scott D.; Chen, Mei-Jin; Dinaut, A. Nicole; Batey, Robert A. Tetrahedron, 1998 , vol. 54, # 17 p. 4223 - 4242

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Citation Number: 7

Abstract

O-alkyl N, O′-arylphosphoramidates were synthesized by reacting phenol and aniline derivatives with alkyldichlorophosphites to form phosphoramidites followed by oxidation with m-CPBA. Selective cleavage of the alkyl group under mild, neutral conditions afforded the corresponding N, O-arylphosphoramidic acids. This methodology was used to synthesize a N, O-arylphosphoramidate transition state analogue for carbamate hydrolysis.