Issue 45, 2013
From the journal:

Chemical Communications

NHC–Cu(i) catalysed asymmetric conjugate silyl transfer to unsaturated lactones: application in kinetic resolution†

Vittorio Pace,‡a   James P. Rae,‡a   Hassan Y. Harba  and  David J. Procter*a  

* Corresponding authors

a School of Chemistry, University of Manchester, Oxford Road, Manchester, UK
E-mail: david.j.procter@manchester.ac.uk

Abstract

The scope of the asymmetric silyl transfer to unsaturated lactones utilising a C2-symmetric NHC–Cu(I) catalyst has been established and kinetic resolutions mediated by silyl transfer have been used to prepare enantiomerically enriched anti-4,5-disubstituted 5-membered lactones. The method has been exploited in an expedient synthesis of (+)-blastmycinone.

Graphical abstract: NHC–Cu(i) catalysed asymmetric conjugate silyl transfer to unsaturated lactones: application in kinetic resolution

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Article information

DOI
https://doi.org/10.1039/C3CC42160K
Article type
Communication
Submitted
25 Mar 2013
Accepted
15 Apr 2013
First published
15 Apr 2013
This article is Open Access
Creative Commons BY license

Chem. Commun., 2013,49, 5150-5152

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NHC–Cu(I) catalysed asymmetric conjugate silyl transfer to unsaturated lactones: application in kinetic resolution

V. Pace, J. P. Rae, H. Y. Harb and D. J. Procter, Chem. Commun., 2013, 49, 5150 DOI: 10.1039/C3CC42160K

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