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

The Journal of Organic Chemistry
Lauren C IrwinMichael A Kerr

Abstract

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.

References

Feb 9, 2008·Organic Letters·Christian PerreaultAndré B Charette
Oct 23, 2009·Chemical Society Reviews·Cheryl A Carson, Michael A Kerr
Oct 13, 2010·Organic Letters·Michael B Johansen, Michael A Kerr
Dec 20, 2012·Organic Letters·Gergely L TolnaiJérôme Waser
Jul 3, 2013·Organic Letters·Florian de NanteuilJérôme Waser
Nov 22, 2013·Chemical Society Reviews·Marchello A CavittStefan France
Apr 29, 2014·Angewandte Chemie·Tobias F SchneiderDaniel B Werz
Oct 11, 2014·Angewandte Chemie·Pier Alexandre ChampagneJean-François Paquin
Nov 27, 2014·Organic & Biomolecular Chemistry·Huck K GroverMichael A Kerr

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Citations

Jul 10, 2019·Chemistry : a European Journal·André U AugustinDaniel B Werz
Nov 1, 2018·ChemPlusChem·Silvia González-Pelayo, Luis A López
Jan 21, 2021·Organic & Biomolecular Chemistry·Koena Ghosh, Subhomoy Das
Mar 4, 2021·The Journal of Organic Chemistry·Denis D BorisovYury V Tomilov
Dec 6, 2019·The Journal of Organic Chemistry·Maksim A BoichenkoOlga A Ivanova

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