Synthesis

β-Tosylethylhydroxylamine: Preparation and use as a hydroxylamine equivalent in amidyl radical-olefin cyclizations

GD Artman Iii, JH Waldman, SM Weinreb

Index: Artman III, Gerald D.; Waldman, Jacob H.; Weinreb, Steven M. Synthesis, 2002 , # 14 p. 2057 - 2063

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Citation Number: 17

Abstract

Abstract An efficient three-step procedure has been developed for synthesis of β- tosylethylhydroxylamine from commercially available starting material. This compound forms hydroxamic acids which undergo amidyl radical-olefin cyclizations promoted by diethyl chlorophosphite to give functionalized β-tosylethyl-protected lactams, which can be deprotected under mild basic conditions.

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