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Synlett 2015; 26(15): 2067-2087
DOI: 10.1055/s-0034-1380862
DOI: 10.1055/s-0034-1380862
account
Stereodivergent Asymmetric Reactions Catalyzed by Brucine Diol
Further Information
Publication History
Received: 27 March 2015
Accepted after revision: 23 April 2015
Publication Date:
30 July 2015 (online)
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 endo-Selective [3+2]-Cycloaddition Reactions
4 Cooperative Catalysis Approaches
5 Outlook
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