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Synfacts 2009(3): 0333-0333
DOI: 10.1055/s-0028-1087720
DOI: 10.1055/s-0028-1087720
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
New Chiral DMAP-Catalysts
T. A. Duffey, S. A. Shaw, E. Vedejs*
University of Michigan, Ann Arbor, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
19. Februar 2009 (online)
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.