Transition-Metal-Catalyzed Enantioselective α-Arylation of Carbonyl Compounds to Give Tertiary Stereocenters

Abstract

Enantioenriched α-aryl carbonyl compounds are ubiquitous in natural products and biologically active compounds. Their synthesis has been explored over the last few decades and several methods now exist that allow for the enantioselective formation of a C(sp³)-C(sp²) bond in the α-position to a carbonyl group. However, although the formation of quaternary stereocenters has been fairly well established, the enantioselective formation of tertiary stereocenters proved more challenging due to facile product post-reaction racemization. In this short review, we summarize the methods reported to date for the asymmetric α-arylation of enolates and analogues that rely on transition-metal catalysis.

1 Introduction

2 Nucleophile Pre-activation

3 Activation via Aminocatalysis

4 Formation of Constrained Stereocenters

5 Concluding Remarks

Key words

α-arylation of carbonyl compounds - transition-metal catalysis - enantioselective catalysis - aminocatalysis - tertiary stereocenters

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