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New Phenylglycine‐Derived Primary Amine Organocatalysts for the Preparation of Optically Active Warfarin
Author(s) -
Kristensen Tor E.,
Vestli Kristian,
Hansen Finn K.,
Hansen Tore
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900664
Subject(s) - chemistry , primary (astronomy) , amine gas treating , optically active , enantiomer , catalysis , organic chemistry , combinatorial chemistry , enantiomeric excess , acetic acid , cinchona , warfarin , enantioselective synthesis , physics , astronomy , medicine , atrial fibrillation , cardiology
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.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)