Tetrahedron letters

Substrate steric effects in enantioselective Lewis acid promoted free radical reactions

JH Wu, G Zhang, NA Porter

Index: Wu, Jason Hongliu; Zhang, Guiru; Porter, Ned A. Tetrahedron Letters, 1997 , vol. 38, # 12 p. 2067 - 2070

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Citation Number: 49

Abstract

High to moderate levels of stereoselectivity are observed in chiral Lewis acid promoted allyl transfer reactions of radicals substituted α to oxazolidinones. Similar selectivity patterns are observed for reactions in which such radicals are generated by addition to an acrylimide or by reactions in which the same radical is generated from the corresponding bromide. A good correlation is obtained for selectivity vs. the Taft steric parameter for the alkyl group ...