Synthesis 2018; 50(19): 3843-3861
DOI: 10.1055/s-0037-1609583
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Copper-Catalyzed Asymmetric Hydroboration of Electron-Deficient Alkenes: Methodologies and Mechanism

Jing-Biao Chen
Centre for Sustainable Chemical Processes, Department of Chemistry, Durham University, Science Laboratories, South Road, Durham DH1 3LE, UK   Email: [email protected]
,
Centre for Sustainable Chemical Processes, Department of Chemistry, Durham University, Science Laboratories, South Road, Durham DH1 3LE, UK   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 11 June 2018

Accepted: 15 June 2018

Publication Date:
23 July 2018 (online)


Abstract

The efficient synthesis of enantioenriched organoboron compounds has been recognized as an important topic in recent years. As an update review, this article aims to select key achievements in copper-catalyzed, electron-deficient alkene enantioselective hydroboration methodologies since the beginning of 2017. In addition, it covers relevant mechanistic investigations developed over the last six years, as well as total synthesis applications for preparing 1,3-diols as important medicinal intermediates.

1 Introduction

2 Methodologies for Copper-Catalyzed Hydroboration

2.1 α,β-Unsaturated Ketones and Imines

2.2 α,β-Unsaturated Esters and Cyanides

2.3 Aryl Alkenes and Alkyl Alkenes

3 Mechanistic Investigations on the Copper-Catalyzed Hydroboration

3.1 A Cu–BX2 Intermediate

3.1.1 Experimental Analysis

3.1.2 Borylative Difunctionalization Methodologies

3.1.3 Density Functional Theory

3.2 A Cu–H Intermediate

3.3 Other Mechanistic Proposals

4 Synthetic Applications: Chiral 1,3-Diols

5 Conclusions and Outlook

 
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