Construction of Benzylic Stereogenic Carbon Centers through Enantioselective Arylation Reactions

Abstract

Compounds bearing chiral benzylic stereocenters are important and frequently occur in natural products and drug molecules. In this account, we discuss our recent results on the construction of ­benzylic stereogenic centers based on enantioselective arylation and related domino sequences, mainly including asymmetric Friedel–Crafts alkylation reactions and asymmetric Heck reactions.

1 Introduction

2 The Catalytic Asymmetric Friedel–Crafts Alkylation Reaction

2.1 Reactions of Electron-Deficient Alkenes

2.2 Reactions of Active Ketimines

2.3 Reactions of Nitrones

2.4 Reactions of Aziridines

3 The Asymmetric Heck Reaction

3.1 Dearomative Heck Reactions and Related Domino Sequences

3.2 Heck Reactions of in situ Formed Enamines

4 Conclusion and Outlook

Key words

benzylic stereocenter - arylation - Friedel–Crafts reaction - Heck reaction - asymmetric catalysis

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