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Synfacts 2005(2): 0234-0234  
DOI: 10.1055/s-2005-916080
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Peptide-Based Catalysts for Alkenylzinc Addition to Aldehydes

Contributor(s): Mark Lautens, Y. Eric Fang
C. M. Sprout, M. L. Richmond, C. T. Seto*
Brown University, rhode island, USA
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Publication History

Publication Date:
25 October 2005 (online)

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Significance

Allylic alcohols were obtained in good yield and excellent ee via an alkenylzinc addition to an aldehyde using a peptide-based catalyst. The optimal structure of the catalyst was deduced from a 52-membered library using a solid-phase combinatorial approach. The range of aldehydes was broad, including aryl, alkyl, and alkenyl aldehydes. Electron-poor aldehydes generally gave the highest ee while sterically hindered and alkenyl aldehydes gave lower ee.