Organic Chemistry Portal



A Novel Class of Tunable Zinc Reagents (RXZnCH2Y) for Efficient Cyclopropanation of Olefins

Jon C. Lorenz, Jiang Long, Zhiqiang Yang, Song Xue, Yinong Xie and Yian Shi*

*Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, Email:

J. C. Lorenz, J. Long, Z. Yang, S. Xue, X. Xie, Y. Shi, J. Org. Chem., 2004, 69, 327-334.

DOI: 10.1021/jo030312v


A class of zinc reagents (RXZnCH2Y) is very effective for the cyclopropanation of olefins. The reactivity and selectivity of these reagents can be regulated by tuning the electronic and steric nature of the RX group. A reasonable level of enantioselectivity was obtained for the cyclopropanation of unfunctionalized olefins with chiral (iodomethyl)zinc species.

see article for more examples

Key Words

Cyclopropanation, Simmons-Smith Reaction, Organozinc Compounds

ID: J42-Y2004-140