A stereochemical model for merged 1, 2-and 1, 3-asymmetric induction in diastereoselective Mukaiyama aldol addition reactions and related processes

DA Evans, MJ Dart, JL Duffy…

Index: Evans, David A.; Dart, Michael J.; Duffy, Joseph L.; Yang, Michael G. Journal of the American Chemical Society, 1996 , vol. 118, # 18 p. 4322 - 4343

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Citation Number: 334

Abstract

A systematic investigation of the direction and degree of stereoselectivity in aldol addition reactions is presented involving achiral unsubstituted metal enolate and enolsilane nucleophiles and chiral aldehydes. The BF3⊙ OEt2 mediated Mukaiyama aldol reaction with α-unsubstituted, β-alkoxy aldehydes afforded good levels of 1, 3-anti induction in the absence of internal aldehyde chelation. The level of 1, 3-induction was found to be ...