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Synfacts 2010(10): 1194-1194
DOI: 10.1055/s-0030-1258668
DOI: 10.1055/s-0030-1258668
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Chiral Phosphoric Acid Catalyzed Direct Aldol Reactions of Glyoxylates
G. Pousse, F. Le Cavelier, L. Humphreys, J. Rouden, J. Blanchet*
Université de Caen, France and GlaxoSmithKline, Stevenage, UK
Further Information
Publication History
Publication Date:
22 September 2010 (online)
Significance
A Brønsted acid catalyzed direct asymmetric aldol reaction of ketones with glyoxylates is reported. Chiral phosphoric acid 1 was found to be a suitable catalyst for the reaction of ethylglyoxylate with various ketones. The corresponding aldol products were obtained in moderate to good enantioselectivities and good yields. Also the recyclability of the catalyst was demonstrated. The syn-diastereoselectivity of this method complements analogous sec-amine-catalyzed reactions.