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

Joshua V. Ruppel, Ted J. Gauthier, Nicole L. Snyder, Jason A. Perman and X. Peter Zhang*

*Department of Chemistry, University of South Florida, Tampa, Florida 33620-5250, and Department of Chemistry, Hamilton College, Clinton, New York 13323, Email: pzhangcas.usf.edu

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

DOI: 10.1021/ol9005882 (free Supporting Information)

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Abstract

[Co(P1)] is an effective catalyst for asymmetric cyclopropanation of various olefins with succinimidyl diazoacetate, providing the desired cyclopropane succinimidyl esters in high yields and excellent diastereo- and enantioselectivity. The cyclopropane succinimidyl esters serve for the synthesis of optically active cyclopropyl carboxamides.

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

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

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Key Words

Cyclopropanes

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ID: J54-Y2009-1650