4.8 Article

Mechanism of the gold-catalyzed cyclopropanation of alkenes with 1,6-enynes

Journal

CHEMICAL SCIENCE
Volume 2, Issue 1, Pages 141-149

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c0sc00335b

Keywords

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Funding

  1. MICINN [CTQ2010-16088/BQU, CTQ2008-06866-C02-02CSD2006-0003, CSD2006-0003]
  2. FPI
  3. MEC
  4. AGAUR [2009 SGR 47, 2009 SGR 259]
  5. ICIQ Foundation

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The gold(I)-catalyzed intermolecular cyclopropanation of alkenes with 1,6-enynes is an electrophilic process, which is mechanistically related to the well-known Simmons-Smith reaction proceeding through zinc carbenoids. This cyclopropanation is stereospecific, even in cases where the reaction was found to proceed stepwise.

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