The Development of Asymmetric Primary Amine Catalysts Based on Cinchona Alkaloids

Abstract

Primary amines derived from natural cinchona alkaloids are demonstrated to be excellent catalysts for a number of asymmetric reactions of carbonyl compounds. In comparison with chiral secondary amines, these primary amines exhibit superior catalytic efficacy in the Michael addition and cycloaddition reactions of α,β-unsaturated ketones, and high stereoselectivities have been generally achieved. Additionally, they can also be effectively applied in the enamine catalysis of carbonyl compounds, even in the reactions of rarely used aryl ketones.

1 Introduction

2 Asymmetric Michael Addition Reactions of
α,β-Unsaturated Ketones

3 Asymmetric Pericyclic Reactions of α,β-Unsaturated ­Ketones

4 Asymmetric Reactions of Carbonyl Compounds by ­Enamine Activation

5 Summary

Key words

asymmetric organocatalysis - primary amines - cinchona alkaloids - iminium ions - enamines

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