Issue 3, 2011
From the journal:

Organic & Biomolecular Chemistry

Asymmetric copper-catalysed intramolecular C–H insertion reactions of α-diazo-β-keto sulfones†

Catherine N. Slatterya  and  Anita R. Maguire*b  

* Corresponding authors

a Department of Chemistry and Analytical and Biological Chemistry Research Facility, University College Cork, Ireland

b Department of Chemistry, School of Pharmacy and Analytical and Biological Chemistry Research Facility, University College Cork, Ireland
E-mail: a.maguire@ucc.ie
Fax: +353-(0)21-4274097
Tel: +353-21-4902125

Abstract

Asymmetric copper-catalysed intramolecular C–H insertion reactions of a series of α-diazo-β-keto sulfones are reported. Enantioselectivities of up to 82% ee were achieved in moderate to good yield. These results represent the highest level of enantiocontrol achieved to date for a copper-catalysed cyclopentanone synthesis via C–H insertion.

Graphical abstract: Asymmetric copper-catalysed intramolecular C–H insertion reactions of α-diazo-β-keto sulfones

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Article information

DOI
https://doi.org/10.1039/C0OB00914H
Article type
Communication
Submitted
21 Oct 2010
Accepted
15 Nov 2010
First published
16 Nov 2010

Org. Biomol. Chem., 2011,9, 667-669

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Asymmetric copper-catalysed intramolecular C–H insertion reactions of α-diazo-β-keto sulfones

C. N. Slattery and A. R. Maguire, Org. Biomol. Chem., 2011, 9, 667 DOI: 10.1039/C0OB00914H

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