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Diasteroselective Preparation of Cyclopropanols Using Methylene Bis(iodozinc)

Kevin Cheng, Patrick J. Carroll and Patrick J. Walsh*

*Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States, Email: pwalshsas.upenn.edu

K. Cheng, P. J. Carroll, P. J. Walsh, Org. Lett., 2011, 13, 2346-2349.

DOI: 10.1021/ol200597h (free Supporting Information)


Abstract

The reaction of bimetallic CH2(ZnI)2 with α-chloroaldehydes enables a diastereoselective synthesis of trans-2-substituted cyclopropanols in very good yields and dr’s. The high trans-selectivity resulted from equilibration of the cyclopropoxide intermediates.

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Key Words

cyclopropanols


ID: J54-Y2011-1360