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Development of Highly Diastereo- and Enantioselective Direct Asymmetric Aldol Reaction of a Glycinate Schiff Base with Aldehydes Catalyzed by Chiral Quaternary Ammonium Salts

Takashi Ooi, Minoru Kameda, Mika Taniguchi and Keiji Maruoka*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan, Email: maruokakuchem.kyoto-u.ac.jp

T. Ooi, M. Kameda, M. Taniguchi, K. Maruoka, J. Am. Chem. Soc., 2004, 126, 9685-9694.

DOI: 10.1021/ja048865q (free Supporting Information)


Abstract

A highly efficient direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes has been achieved under mild biphasic conditions with excellent stereochemical control, using a chiral quaternary ammonium salt as a phase-transfer catalyst.

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Key Words

Aldol Addition, Organocatalysis, Phase Transfer Catalysis, O'Donnell Amino Acid Synthesis


ID: J48-Y2004-1640