Recent Advances in the Catalytic Asymmetric Construction of Phosphorus-Substituted Quaternary Carbon Stereocenters

Long Chen

doi:10.1055/s-0036-1590958

Synthesis, Table of Contents

Synthesis 2018; 50(03): 440-469
DOI: 10.1055/s-0036-1590958

review

Recent Advances in the Catalytic Asymmetric Construction of Phosphorus-Substituted Quaternary Carbon Stereocenters

Long Chen*

Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, 168 Hua Guan Road, Chengdu 610052, P. R. of China Email: chenlongl@cdu.edu.cn

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Abstract

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Abstract

Phosphorus-substituted quaternary carbon stereocenters exist widely in drugs and biologically active compounds. Catalytic asymmetric synthesis of such quaternary carbon stereogenic centers is of significant importance, with four synthetic strategies being established. This review summarizes the recent progress in this field, including the advantages and limitations of each strategy, briefly discusses the reaction mechanisms and challenges, and outlines synthetic opportunities still open.

1 Introduction

2 Asymmetric Hydrophosphonylation

3 Asymmetric Electrophilic Phosphination

4 Asymmetric Functionalization of P-Substituted Methine Compounds

5 Asymmetric Addition to α-Keto- or α-Ketiminophosphonates

6 Conclusion

Key words

phosphorus-substituted quaternary carbon stereocenters - enantioselective C–P bond forming reactions - organophosphorus compounds - organocatalysis - metal catalysis

Full Text

References

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