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

Éric Lévesque, Sébastien R. Goudreau and André B. Charette*

*Centre in Green Chemistry and Catalysis, FAS-Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada, H3C 3J7, Email: andre.charetteumontreal.ca

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

DOI: 10.1021/ol500267w (free Supporting Information)



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Abstract

The Simmons-Smith reaction is a powerful method to access cyclopropanes with various substitution patterns. The high reactivity of aryldiazomethanes toward zinc halides generates aryl-substituted carbenoids catalytically. These carbenoids cyclopropanate various alkenes diastereoselectively, including unfunctionalized substrates such as styrenes. The zinc catalyst can be modified to tolerate the use of free allylic alcohols.

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

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


Key Words

Simmons-Smith Reaction, Cyclopropanes


ID: J54-Y2014