Stereoselective Metal-Catalyzed C–C Bond Coupling Reactions by Stereoconvergence, Dynamic Kinetic Asymmetric Transformation, or Dynamic Kinetic Resolution

Joanna Wencel-Delord; Françoise Colobert

doi:10.1055/s-0035-1562512

Synthesis, Table of Contents

Synthesis 2016; 48(18): 2981-2996
DOI: 10.1055/s-0035-1562512

short review

Stereoselective Metal-Catalyzed C–C Bond Coupling Reactions by Stereoconvergence, Dynamic Kinetic Asymmetric Transformation, or Dynamic Kinetic Resolution

Joanna Wencel-Delord*

Laboratoire de chimie moléculaire (UMR CNRS 7509), University of Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg, France Email: francoise.colobert@unistra.fr

,

Françoise Colobert*

Laboratoire de chimie moléculaire (UMR CNRS 7509), University of Strasbourg, ECPM, 25 rue Becquerel, 67087 Strasbourg, France Email: francoise.colobert@unistra.fr

› Author Affiliations

Abstract

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Abstract

The development of stereoselective metal-catalyzed cross-coupling reactions over the past 30 years has revolutionized the way in which C–C, C–N, and C–X bonds are formed in an enantiomerically pure form. In particular asymmetric reactions that transform racemic substrates into enantioenriched products in high, ideally quantitative, yields are particularly appealing. Consequently, many deracemization processes have been developed, implying conceptually diverse strategies such as dynamic kinetic asymmetric transformation (DYKAT), dynamic kinetic resolution (DKR), and stereoconvergence. In this review the most recent achievements in dynamic metal-catalyzed cross couplings of racemic substrates are collected and discussed according to the nature of the deracemization step.

1 Introduction

2 Deracemization by Dynamic Kinetic Resolution (DKR)/Dynamic Kinetic Asymmetric Transformation (DYKAT)

2.1 DKR towards the Control of Central Chirality

2.2 DYKAT towards the Control of Central Chirality

2.3 DKR/DYKAT towards the Control of Axial Chirality

3 Deracemization Involving a Stereoconvergent Transformation

4 Conclusion

Key words

asymmetric reactions - stereoconvergence - dynamic kinetic resolution - dynamic kinetic asymmetric transformation - deracemization

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References

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