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Synfacts 2006(2): 0164-0164  
DOI: 10.1055/s-2005-924799
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Brønsted Acid-Catalyzed Imine Amidation

Contributor(s): Benjamin List, Subhas Chandra Pan
G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla*
University of Mississipi, USA
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Publikationsverlauf

Publikationsdatum:
23. Januar 2006 (online)

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Significance

Asymmetric Brønsted acid catalysis is an emerging area in organocatalysis. Here the authors report a highly enantioselective amidation of aryl-substituted N-Boc imines using a VAPOL-derived phosphoric acid catalyst. Good yields (>80%) and enantioselectivities in the range of 73-99% are obtained for a number of aromatic and heteroaromatic imines.