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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, Email: rjkt1york.ac.uk

R. J. Paxton, R. J. K. Taylor, Synlett, 2007, 633-637.

DOI: 10.1055/s-2007-967966


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Abstract

A new procedure for the cyclopropanation of enones and related systems employs trimethylsulfoxonium iodide and an organic base to generate dimethylsulfoxonium methylide in situ. Activated alcohols are converted directly into cyclopropyl ketones by a one-pot tandem oxidation-cyclopropanation sequence.

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gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

M. G. Edwards, R. J. Paxton, D. S. Pugh, A. C. Whitwood, R. J. K. Taylor, Synthesis, 2008, 3279-3288.


Key Words

Corey-Chaykowsky Reaction, cyclopropanes, cyclopropanations, tandem oxidation procedures, one-pot procedures, manganese(IV) oxide


ID: J60-Y2007-0550