4.5 Article

New Phenylglycine-Derived Primary Amine Organocatalysts for the Preparation of Optically Active Warfarin

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 30, Pages 5185-5191

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900664

Keywords

Amines; Amino alcohols; Asymmetric synthesis; Michael addition; Organocatalysis

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In this work we present new, fully synthetic phenylglycine-derived primary amine organocatalysts useful for the one-step preparation of optically active warfarin, an important anticoagulant, Both enantiomeric forms of the catalysts are equally available and can be prepared by robust procedures without recourse to chromatographic purification. Together with a co-catalyst, particularly acetic acid or 2,4-dinitrophenol, they can furnish warfarin in approximately 80% ee and represent inexpensive alternatives to other primary amine organocatalysts such as the chiral diamines and Cinchona-derived primary amines. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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