Synthesis 2021; 53(17): 2961-2975
DOI: 10.1055/s-0040-1720406
special topic
Bond Activation – in Honor of Prof. Shinji Murai

Enantioselective Intermolecular Murai-Type Alkene Hydroarylation Reactions

Timothy P. Aldhous
a   School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK
b   Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK
,
Raymond W. M. Chung
b   Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK
,
Andrew G. Dalling
a   School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK
,
John F. Bower
b   Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK
› Author Affiliations
We thank the European Research Council [Grant 639594 (CatHet) and Grant 863799 (ChiCC)], the University of Bristol, and the University of Liverpool for funding. We also thank the Bristol Chemical Synthesis Centre for Doctoral Training, funded by the EPSRC (EP/L015366/1), and AstraZeneca for a studentship (to T.P.A.).


Abstract

Strategies that enable the efficient assembly of complex building blocks from feedstock chemicals are of paramount importance to synthetic chemistry. Building upon the pioneering work of Murai and co-workers in 1993, C–H-activation-based enantioselective hydroarylations of alkenes offer a particularly promising framework for the step- and atom-economical installation of benzylic stereocenters. This short review presents recent intermolecular enantioselective Murai-type alkene hydroarylation methodologies and the mechanisms by which they proceed.

1 Introduction

2 Enantioselective Hydroarylation Reactions of Strained Bicyclic Alkenes

3 Enantioselective Hydroarylation Reactions of Electron-Rich Acyclic Alkenes

4 Enantioselective Hydroarylation Reactions of Electron-Poor Acyclic Alkenes

5 Enantioselective Hydroarylation Reactions of Minimally Polarized Acyclic Alkenes

6 Conclusion and Outlook



Publication History

Received: 15 March 2021

Accepted after revision: 15 April 2021

Article published online:
25 May 2021

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