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

---

see article for more reactions

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.

see article for more examples

---

---

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