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
J. Am. Chem. Soc., 2005, 127 (38), pp 13138–13139
DOI: 10.1021/ja0539239
Publication Date (Web): September 2, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, pwalsh@sas.upenn.edu

Abstract

Abstract Image

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 involves asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselective cyclopropanation. Route 2 parallels route 1, except that iodoform is used to generate the zinc carbenoid, and the products are iodocyclopropyl alcohols. Route 3 entails asymmetric vinylation of an aldehyde with divinylzinc reagents and subsequent diastereoselective cyclopropanation.

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History

  • Published In Issue September 28, 2005
  • Received June 14, 2005

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