Synlett 2015; 26(15): 2067-2087
DOI: 10.1055/s-0034-1380862
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© Georg Thieme Verlag Stuttgart · New York

Stereodivergent Asymmetric Reactions Catalyzed by Brucine Diol

Hun Young Kim
Center for Metareceptome Research, College of Pharmacy, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 156-756, Republic of Korea   Email: kyungsoooh@cau.ac.kr
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Kyungsoo Oh*
Center for Metareceptome Research, College of Pharmacy, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 156-756, Republic of Korea   Email: kyungsoooh@cau.ac.kr
› Author Affiliations
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