The Stereochemical Course of Intramolecular Michael Reactions

EE Kwan, JR Scheerer, DA Evans

Index: Kwan, Eugene E.; Scheerer, Onathan R.; Evans, David A. Journal of Organic Chemistry, 2013 , vol. 78, # 1 p. 175 - 203

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Citation Number: 9

Abstract

We present a general model for understanding the stereochemical course of intramolecular Michael reactions. We show that the addition of β-ketoester enolates to α, β-unsaturated esters and imides bearing adjacent stereocenters (X, Y= H, Me, OR) leads to high levels of asymmetric induction. Reinforcing and nonreinforcing stereochemical relationships are evaluated from the syn and anti reactant diastereomers. On the basis of synthetic, ...