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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 AffiliationsWe 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.).
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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

Key words

enantioselective - hydroarylation - C–H activation - catalysis - transition metal


Publication History

Received: 15 March 2021

Accepted after revision: 15 April 2021

Article published online:
25 May 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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