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Preparation of a Storable Zinc Carbenoid Species and Its Application in Cyclopropanation, Chain Extension, and [2,3]-Sigmatropic Rearrangement Reactions

Arnaud Voituriez, Lucie E. Zimmer and André B. Charette

*Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, QC H3C 3J7, Canada, Email:

A. Voituriez, L. E. Zimmer, A. B. Charette, J. Org. Chem., 2010, 75, 1244-1250.

DOI: 10.1021/jo902618e (free Supporting Information)


A phosphate carbenoid (BuO)2P(O)OZnCH2I undergoes very slow degradation in solution and can be stored for several weeks at -20°C. Its reactivity was tested with cyclopropanation of alkenes, chain extension of 1,3-diketones and [2,3]-sigmatropic rearrangement reactions.

see article for more examples

Improved Zinc-Catalyzed Simmons-Smith Reaction: Access to Various 1,2,3-Trisubstituted Cyclopropanes

E. Lévesque, S. R. Goudreau, A. B. Charette, Org. Lett., 2014, 16, 1490-1493.

Key Words

Cyclopropanation, Simmons-Smith Reaction

ID: J42-Y2010-0470