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