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A General and Efficient Cobalt(II)-Based Catalytic System for Highly Stereoselective Cyclopropanation of Alkenes with α-Cyanodiazoacetates

Shifa Zhu, Xue Xu, Jason A. Perman and X. Peter Zhang*

*Department of Chemistry, University of South Florida, Tampa, Florida 33620-5250, and School of Chemistry, Email: xpzhangusf.edu

S. Zhu, X. Xu, J. A. Perman, X. P. Zhang, J. Am. Chem. Soc., 2010, 132, 12796-12799.

DOI: 10.1021/ja1056246 (free Supporting Information)



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Abstract

A cobalt(II) complex of a D2-symmetric chiral porphyrin is an effective catalyst for catalyzing asymmetric olefin cyclopropanation with α-cyanodiazoacetates. The reaction is suitable for both aromatic and aliphatic olefins, including electron-rich and poor olefins under mild conditions, affording the desired cyclopropane products in high yields with both high diastereo- and enantioselectivity.


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Asymmetric Co(II)-Catalyzed Cyclopropanation with Succinimidyl Diazoacetate: General Synthesis of Chiral Cyclopropyl Carboxamides

J. V. Ruppel, T. J. Gauthier, N. L. Snyder, J. A. Perman, X. P. Zhang, Org. Lett., 2009, 11, 2273-2276.


Key Words

cyclopropanation


ID: J48-Y2010-2590