Synlett 2014; 25(1): 08-11
DOI: 10.1055/s-0033-1340157
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© Georg Thieme Verlag Stuttgart · New York

Lewis Acid Catalyzed Rearrangement of Furylcarbinols: The Aza- and Oxa-Piancatelli Cascade Reaction

Leoni I. Palmer
Department of Chemistry and Biochemistry, University of California-Santa Barbara, Santa Barbara, CA 93106-9510, USA   Fax: +1(805)8934120   Email: javier@chem.ucsb.edu
,
Javier Read de Alaniz*
Department of Chemistry and Biochemistry, University of California-Santa Barbara, Santa Barbara, CA 93106-9510, USA   Fax: +1(805)8934120   Email: javier@chem.ucsb.edu
› Author Affiliations
Further Information

Publication History

Received: 30 August 2013

Accepted: 24 September 2013

Publication Date:
06 November 2013 (online)

Abstract

The acid-catalyzed rearrangement of furylcarbinols is utilized to access 4,5-substituted cyclopentenones. This cascade transformation began with implementing anilines, as an alternative nucleophile to water as used in the Piancatelli rearrangement, and has currently progressed through an intramolecular rearrangement to the use of alcohols as the nucleophile.

 
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