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

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Department of Chemistry, P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323
Cite this: J. Am. Chem. Soc. 2005, 127, 38, 13138–13139
Publication Date (Web):September 2, 2005
https://doi.org/10.1021/ja0539239
Copyright © 2005 American Chemical Society
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    Abstract

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    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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