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Highly Enantio- and Diastereoselective Tandem Generation of Cyclopropyl Alcohols with up to Four Contiguous Stereocenters

Hun Young Kim, Alice E. Lurain, Patricia García-García, Patrick J. Carroll and Patrick J. Walsh*

*Department of Chemistry, P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, Email: pwalshsas.upenn.edu

H. Y. Kim, A. E. Lurain, P. Garcia-Carcia, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2005, 127, 13138-13139.

DOI: 10.1021/ja0539239 (free Supporting Information)


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Abstract

Three highly enantio- and diastereoselective one-pot procedures for the synthesis of cyclopropyl and iodocyclopropyl alcohols with up to four contiguous stereocenters are reported. Route 1 and 2 involve asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselective cyclopropanation using either diiodomethane or iodoform to generate the zinc carbenoid, leading to cyclopropyl or iodocyclopropyl alcohols, respectively. Route 3 entails asymmetric vinylation of an aldehyde with divinylzinc reagents and subsequent diastereoselective cyclopropanation.

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Highly Enantio- and Diastereoselective One-Pot Synthesis of Acyclic Epoxy Alcohols with Three Contiguous Stereocenters

A. E. Lurain, A. Maestri, A. R. Kelli, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2004, 126, 13608-13609.

Applications of 1-Alkenyl-1,1-Heterobimetallics in the Stereoselective Synthesis of Cyclopropylboronate Esters, Trisubstituted Cyclopropanols and 2,3-Disubstituted Cyclobutanones

M. M. Hussain, H. Li, N. Hussain, M. Ureña, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2009, 131, 6516-6524.


Key Words

Addition, Cyclopropanation


ID: J48-Y2005-2600