Synthesis of β-Hydroxyaldehydes with Stereogenic Quaternary Carbon Centers by Direct Organocatalytic Asymmetric Aldol Reactions

Authors

  • Nobuyuki Mase Prof. Dr.,

    1. Department of Molecular Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Japan
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  • Fujie Tanaka Prof. Dr.,

    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2583 
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  • Carlos F. Barbas III Prof. Dr.

    1. The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2583 
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  • This study was supported in part by the NIH (CA27489) and by The Skaggs Institute for Chemical Biology.

Abstract

original image

Mit einem Fluoreszenzdetektor wurden Katalysatorsysteme aus chiralen Aminen und Säuren für asymmetrische direkte Aldolreaktionen von α,α-Dialkylaldehyden mit Arylaldehyden identifiziert (siehe Schema). Der optimierte Katalysator lieferte das α,α-Dimethyl-Aldolprodukt aus Isobutyraldehyd und p-Nitrobenzaldehyd mit 92 % Ausbeute und 96 % ee. (R1, R2= Alkyl; X=NO2, CN, Br, Cl, OMe, H)

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