Additions to Racemates: A Strategy for Developing Asymmetric Cross-Coupling Reactions

Abstract

In this Account, the authors describe their progress in developing catalytic asymmetric C(sp³)–C(sp³) and C(sp³)–C(sp²) cross-coupling reactions. Whereas most catalytic enantioselective transformations rely on prochiral or meso starting materials, strategies that use racemic starting materials are rare. Key features of these reactions are efficient mechanisms for deracemization. Here, the authors present copper-catalyzed alkylation and rhodium-catalyzed Suzuki–Miyaura-type arylation reactions, their underlying mechanisms, and their applications in complex-molecule syntheses.

Key words

asymmetric catalysis - arylboronic acids - copper catalysis - cross-coupling - rhodium catalysis - Suzuki–Miyaura reaction

Publication History

Received: 01 March 2021

Accepted after revision: 21 March 2021

Article published online:
12 April 2021

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