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Gold-catalyzed diastereoselective synthesis of α-fluoroenones from propargyl acetates

Lookup NU author(s): Dr Matt HopkinsonORCiD

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Abstract

A diastereoselective preparation of -fluoroenones from propargyl acetates has been developed proceeding via a gold-catalyzed rearrangement-fluorination cascade. Control reactions are consistent with a mechanism involving a gold-mediated 3,3-sigmatropic shift followed by a direct, nongold-catalyzed electrophilic fluorination of the allenyl acetate intermediate. © 2010 Georg Thieme Verlag Stuttgart · New York.

Publication metadata

Author(s): Hopkinson MN, Giuffredi GT, Gee AD, Gouverneur V

Publication type: Article

Publication status: Published

Journal: Synlett

Year: 2010

Issue: 18

Pages: 2737-2742

Online publication date: 08/10/2010

ISSN (print): 0936-5214

ISSN (electronic): 1437-2096

Publisher: Georg Thieme Verlag

URL: https://doi.org/10.1055/s-0030-1258992

DOI: 10.1055/s-0030-1258992

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