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