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Synthesis 2018; 50(19): 3843-3861
DOI: 10.1055/s-0037-1609583
DOI: 10.1055/s-0037-1609583
short review
Recent Advances in Copper-Catalyzed Asymmetric Hydroboration of Electron-Deficient Alkenes: Methodologies and Mechanism
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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For applications in pharmaceuticals and bioactive molecules, see:
For selected reviews on borylation and its transformations, see:
For selected reviews relevant to the topic of borylation, see:
For selected reviews on diboration, see:
For selected reviews on borylative bifunctionalization, see:
For selected reviews on C–H borylation, see:
For selected reviews on C–X borylation, see:
For selected literature on Brown hydroboration, see:
For selected reviews on alkene hydroboration, see:
For selected reviews on 1,3-diol synthesis and relevant strategies, see:
For selected examples on alkoxide or hydroxide base anion catalyzed alkene hydroboration, see:
For selected examples of methodologies proposing ‘Cu–BX2’ as borylation intermediates, see:
For selected recent works on copper-catalyzed borylative difunctionalization, see:
For selected relevant literature on DFT studies of catalytic borylation of alkenes, see:
For selected recent methodological and mechanical investigations on the hydrocupration of alkenes, see:
For selected examples on background reactions in alkene hydroboration, see:
For selected examples on NHC activation of diboron compounds, see:
For selected examples on the radical mechanism of the borylation of alkenes, see: