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Synfacts 2007(11): 1183-1183
DOI: 10.1055/s-2007-991262
DOI: 10.1055/s-2007-991262
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Conjugate Addition of Organometallic Reagents to Acyclic Dienones
R. Šebesta, M. G. Pizzuti, A. J. Minnaard*, B. L. Feringa*
University of Groningen, The Netherlands and Comenius University, Bratislava, Slovakia
Further Information
Publication History
Publication Date:
24 October 2007 (online)
Significance
The Feringa group describes the conjugate addition to acyclic dienones. This is an interesting class of compounds for which controlled single addition products are obtained in high yields. The products can be used for a moderately diastereoselective second addition or be subjected to ring-closing metathesis to generate substituted cyclopentenones. The diastereoselective second addition of the allyl moiety is likely due to stereoselective generation of the intermediary enolate.