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Synlett 2005(20): 3075-3078  
DOI: 10.1055/s-2005-922752
LETTER
© Georg Thieme Verlag Stuttgart · New York

Intramolecular Prins Reactions of Vinylcyclopropanes with Aldehydes and Ketones: A New Synthesis of Semicyclic Conjugated Dienes

Yinghui Liu, Nabi A. Magomedov*
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA
Fax: +1(585)2760205; e-Mail: magomedov@chem.rochester.edu;
Further Information

Publication History

Received 25 August 2005
Publication Date:
28 November 2005 (online)

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Abstract

Carbonyl compounds bearing pendant vinylcyclopropanes react with sulfonic acids to produce semicyclic conjugated dienes. These functionalized dienes can be readily elaborated into complex polycyclic compounds.

Key words

vinylcyclopropane - cyclizations - ring opening - eliminations - conjugated diene

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5

The use of methanesulfonic acid in the reaction with 1 produced the corresponding mesylate in 48% yield.