4.7 Article

Nucleophilic Opening of Donor-Acceptor Cyclopropanes with Indoles via Hydrogen Bond Activation with 1,1,1,3,3,3-Hexafluoroisopropanol

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 11, Pages 6235-6242

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00894

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Funding

  1. Natural Sciences and Engineering Research Council of Canada
  2. Ontario Graduate Scholarship

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The treatment of donor acceptor cyclopropanes with the a strong hydrogen bond donor, HFIP, activated the cyclopropanes (via presumed hydrogen bonding) toward homo-Michael additions with indoles as the nucleophiles. This reaction proceeded without the need for high pressure or catalysis.

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