Stereodivergent Asymmetric Reactions Catalyzed by Brucine Diol

Hun Young Kim; Kyungsoo Oh

doi:10.1055/s-0034-1380862

Synlett, Table of Contents

Synlett 2015; 26(15): 2067-2087
DOI: 10.1055/s-0034-1380862

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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

,

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

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Abstract

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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

Key words

aldol reaction - asymmetric catalysis - brucine diol - enantioselectivity - stereoselectivity

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References

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