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Synfacts 2009(3): 0333-0333  
DOI: 10.1055/s-0028-1087720
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

New Chiral DMAP-Catalysts

Contributor(s): Benjamin List, Kristina Zumbansen
T. A. Duffey, S. A. Shaw, E. Vedejs*
University of Michigan, Ann Arbor, USA
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

Vedejs and co-workers report an enantioselective rearrangement of N-diphenyl­acetyl indolyl acetates and carbonates to the corresponding oxindoles using new chiral DMAP derivatives. Remarkably, upon changing the catalyst from 1 to 2 and the migrating groups, the reaction afforded the oxindole with an opposite configuration. The synthetic potential of the corresponding products is demonstrated by the facile deprotection and the easy conversion into the corresponding Baeyer-Villiger product.