4.4 Article

Calcium-catalyzed Friedel-Crafts addition of 1-methylindole to activated cyclopropanes

Journal

TETRAHEDRON LETTERS
Volume 55, Issue 38, Pages 5280-5282

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.07.108

Keywords

Cyclopropane; Indole; Calcium catalysis; Friedel-Crafts

Funding

  1. Donors of theAmerican Chemical Society Petroleum Research Fund
  2. University of Richmond

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The synthesis of gamma-indolyl malonates was achieved through the addition of indoles to activated cyclopropanes. These Friedel-Crafts reactions were catalyzed by calcium bis(trifluoromethanesulfonimide), Ca(NTf2)(2). The addition proceeded with complete regioselectivity and in good to excellent yields. Optimization of the reaction conditions and investigation into the scope of the reaction with regard to substitution on cyclopropane are reported. (C) 2014 Elsevier Ltd. All rights reserved.

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