Journal of the American Chemical Society

The role of the achiral template in enantioselective transformations. Radical conjugate additions to α-methacrylates followed by hydrogen atom transfer

MP Sibi, JB Sausker

Index: Sibi, Mukund P.; Sausker, Justin B. Journal of the American Chemical Society, 2002 , vol. 124, # 6 p. 984 - 991

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Citation Number: 60

Abstract

We have evaluated various achiral templates (1a-g, 10, and 16) in conjunction with chiral Lewis acids in the conjugate addition of nucleophilic radicals to α-methacrylates followed by enantioselective H-atom transfer. Of these, a novel naphthosultam template (10) gave high enantioselectivity in the H-atom-transfer reactions with ee's up to 90%. A chiral Lewis acid derived from MgBr2 and bisoxazoline (2) gave the highest selectivity in the ...