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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: yianlamar.colostate.edu

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

DOI: 10.1021/jo030312v


Abstract

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.

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Key Words

Cyclopropanation, Simmons-Smith Reaction, Organozinc Compounds


ID: J42-Y2004-140