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Lewis Acid-Catalyzed Conjugate Additions of Silyloxyallenes: A Selective Solution to the Intermolecular Rauhut-Currier Problem

Troy E. Reynolds, Michael S. Binkley and Karl A. Scheidt

*Department of Chemistry, Northwestern University, Evanston, Illinois 60208, Email: scheidtnorthwestern.edu

T. E. Reynolds, M. S. Binkley, K. A. Scheidt, Org. Lett., 2008, 10, 2449-2452.

DOI: 10.1021/ol800745q (free Supporting Information)


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Abstract

Silyloxyallenes serve as highly useful α-acylvinyl anion equivalents, that undergo conjugate additions to alkylidene malonates in the presence of Sc(OTf)3 as catalyst. The reaction delivers intermolecular Rauhut-Currier products in excellent yields and regioselectivities for a wide scope of substrates.

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Key Words

Enones, 1,4-Additions


ID: J54-Y2008-1640