LETTER	Synlett 2007: 0633-0637   DOI: 10.1055/s-2007-967966
© Georg Thieme Verlag Stuttgart · New York
Improved Dimethylsulfoxonium Methylide Cyclopropanation Procedures, Including a Tandem Oxidation Variant
Richard J. Paxton, Richard J. K. Taylor*
University of York, Department of Chemistry, Heslington, York, YO10 5DD, UK Fax: +44(1904)434523; e-Mail: rjkt1@york.ac.uk;
Received 8 November 2006

Abstract

A new procedure for the cyclopropanation of α,β-unsaturated carbonyl compounds and related systems is described which employs trimethylsulfoxonium iodide and an organic base in acetonitile to generate dimethylsulfoxonium methylide in situ; in addition, preliminary results are described in which activated alcohols are converted directly into cyclopropyl ketones by a one-pot tandem oxidation-cyclopropanation sequence.

Key words

cyclopropanes - cyclopropanations - tandem oxidation procedures - one-pot procedures