Asymmetric Vinylogous Mannich Reaction of Silyloxy Furans with <i>N</i>-<i>tert</i>-Butanesulfinyl Ketimines
Organic LettersPublished 17 January 2014
V. U. Bhaskara Rao, Amol P. Jadhav, Dnyaneshwar N. Garad, Ravi P. Singh
Citations43
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Abstract
A highly regio- and diastereoselective TMSOTf promoted vinylogous Mannich reaction for the synthesis of chiral quaternary 3-aminooxindole butenolides from 2-silyloxy furans and chiral ketimines is described. The method is found to be very efficient and also provides a facile access to sterically challenging 3-aminooxindole butenolides bearing two quaternary centers in continuation. Further, the versatility of the method is demonstrated by the 1,4-addition of nucleophiles on the sterically congested butenolide substructure.
Keywords
Chemistry
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