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Directed Carbozincation Reactions of Cyclopropene Derivatives

Vinod Tarwade, Xiaozhong Liu, Ni Yan and Joseph M. Fox*

*Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, Email:

V. Tarwade, X. Liu, N. Yan, J. M. Fox, J. Am. Chem. Soc., 2009, 131, 5382-5383.

DOI: 10.1021/ja900949n

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A diastereoselective Cu-catalyzed addition of diorganozinc reagents to readily available cyclopropene derivatives is directed by ester and oxazolidinone functions with excellent facial selectivity. The resulting cyclopropylzinc reagents can be captured via stereospecific reactions with electrophiles.

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Studies on the Stability of Cycloprop-2-ene Carboxylate Dianions and Reactions with Electrophiles

L. A. Fisher, J. M. Fox, J. Org. Chem., 2008, 73, 8474-8478.

Key Words

cyclopropanes, cyclopropenes

ID: J48-Y2009-1340