4.8 Article

Diastereoselective Fluorocyclopropanation of Chiral Allylic Alcohols Using an α-Fluoroiodomethylzinc Carbenoid

Journal

ORGANIC LETTERS
Volume 17, Issue 17, Pages 4288-4291

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02097

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Funding

  1. Natural Science and Engineering Research Council of Canada (NSERC)
  2. Canada Research Chair Program
  3. Canada Foundation for Innovation
  4. FRQNT Centre in Green Chemistry and Catalysis
  5. Universite de Montreal

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Chiral fluorocyclopropyl carbinols were synthesized in high diastereoselectivities via a zinc mediated cyclopropanation reaction, using sec-allylic alcohols as simple building blocks. An enantioselective version of this transformation was achieved through in situ formation of chiral allylic zinc sec-alkoxides from the requisite aldehydes using Walsh's protocol.

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