Issue 74, 2012
From the journal:

Chemical Communications

Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes†

Varinder K. Aggarwal,*a   Liam T. Ball,a   Simon Carobene,a   Rickki L. Connelly,a   Matthew J. Hesse,a   Benjamin M. Partridge,a   Philippe Roth,a   Stephen P. Thomasa  and  Matthew P. Webstera  

* Corresponding authors

a School of Chemistry, University of Bristol, Bristol BS8 1TS, UK
E-mail: V.Aggarwal@Bristol.ac.uk
Fax: +44 (0)117 925 1295
Tel: +44 (0)117 954 6315

Abstract

The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation–borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.

Graphical abstract: Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

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Article information

DOI
https://doi.org/10.1039/C2CC32176A
Article type
Communication
Submitted
25 Mar 2012
Accepted
04 May 2012
First published
08 May 2012

Chem. Commun., 2012,48, 9230-9232

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Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

V. K. Aggarwal, L. T. Ball, S. Carobene, R. L. Connelly, M. J. Hesse, B. M. Partridge, P. Roth, S. P. Thomas and M. P. Webster, Chem. Commun., 2012, 48, 9230 DOI: 10.1039/C2CC32176A

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