Stereodivergent Asymmetric Reactions Catalyzed by Brucine Diol

Abstract

This account summarizes the recent efforts in the Oh group toward the development of stereodivergent asymmetric catalysis using a single chiral source, namely brucine diol. Enantiodivergent catalytic approaches are discussed in the context of [3+2]-cycloaddition reactions, aldol-type reactions, and Friedel–Crafts alkylation reactions. Expansion of the brucine diol catalyzed asymmetric reactions is also detailed in diastereodivergent conjugate addition reactions as well as in a cooperative catalysis approach to the aldol reactions of methyl isocyanate. Collectively, the research presented in this account demonstrates the important mechanistic as well as practical significance of single ­chiral-source-based asymmetric catalysis. 1 Introduction 2 Enantiodivergent Approaches 2.1 [3+2]-Cycloaddition Reactions 2.2 Nitro-Aldol Reactions 2.3 Friedel–Crafts Alkylation Reactions 3 Diastereodivergent Approaches 3.1 Conjugate Addition Reactions 3.2 <i>endo</i>-Selective [3+2]-Cycloaddition Reactions 4 Cooperative Catalysis Approaches 5 Outlook