Synthesis 2016; 48(08): 1087-1100
DOI: 10.1055/s-0035-1560406
review
© Georg Thieme Verlag Stuttgart · New York

Recent Progress in Copper-Catalyzed Asymmetric Allylic Substitution Reactions Using Organoboron Nucleophiles

Ryo Shintani*
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 09 December 2015

Accepted after revision: 28 December 2015

Publication Date:
19 February 2016 (online)


Abstract

Recent progress in copper-catalyzed asymmetric allylic substitution reactions with organoboron nucleophiles is reviewed. Wide availability, high functional group compatibility, and mild reaction conditions are the main advantages over conventional highly reactive organometallic nucleophiles. The use of diboron and silylboron reagents for the synthesis of enantioenriched allylboronates and allylsilanes is also included.

1 Introduction

2 Chirality Transfer of Enantioenriched Allylic Substrates with Organoboron­ Nucleophiles

3 Enantioselective Allylic Substitution of Achiral Substrates with Organoboron Nucleophiles

4 Enantioselective Allylic Substitution of Achiral Substrates with Other Boron-Based Nucleophiles

5 Conclusions

 
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