4.7 Article

Spectroscopic characterization of (diiodomethyl)zinc iodide: application to the stereoselective synthesis and functionalization of iodocyclopropanes

Journal

CHEMICAL COMMUNICATIONS
Volume 53, Issue 69, Pages 9606-9609

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7cc04348a

Keywords

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Funding

  1. Natural Science and Engineering Research Council of Canada (NSERC) [RGPIN-06438]
  2. Canada Foundation for Innovation Leaders Opportunity Funds [227346]
  3. Canada Research Chair Program [CRC-227346]
  4. FRQNT Team Grant [PR-190452]
  5. FRQNT Centre in Green Chemistry and Catalysis (CGCC) Strategic Cluster [RS-171310]
  6. Universitede Montreal

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Herein is described an improved synthetic route to enantio- and diastereoenriched iodocyclopropylmethanols using (diiodomethyl)zinc iodide etherate as the active species. The products obtained by this methodology were successfully functionalized by SuzukiMiyaura cross-coupling reactions. A Buchwald-type palladium precatalyst allowed access to highly substituted and stereo-enriched cyclopropanes without requiring a protecting group.

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