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Synfacts 2007(11): 1183-1183  
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

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
R. Šebesta, M. G. Pizzuti, A. J. Minnaard*, B. L. Feringa*
University of Groningen, The Netherlands and Comenius University, Bratislava, Slovakia
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Publikationsdatum:
24. Oktober 2007 (online)

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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.