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Synfacts 2010(5): 0585-0585  
DOI: 10.1055/s-0029-1219675
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

A New Phosphate Zinc Carbenoid

Contributor(s): Paul Knochel, Andreas J. Wagner
A. Voituriez, L. E. Zimmer, A. B. Charette*
Université de Montréal, Canada
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Publikationsdatum:
22. April 2010 (online)

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Significance

(BuO)2P(O)OZnCH2I, a new phosphate carbenoid, shows very slow degradation at -22 ˚C and can be used several weeks after its synthesis. It is shown to be a powerful cyclopropanating agent for protected and unprotected ­allylic alcohols as well as styrenes or unfunctionalized alkenes. Good results are also obtained for the chain extension of 1,3-diketones and for the [2,3]-sigmatropic rearrangement of allylic sulfides.