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Issue 74, 2012
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Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes

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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


Submitted
25 Mar 2012
Accepted
04 May 2012
First published
08 May 2012

Chem. Commun., 2012,48, 9230-9232
Article type
Communication

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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