Enantioselective rearrangement of indolyl carbonates catalyzed by chiral DMAP-N-oxides

Bifunctional chiral DMAP-N-oxides have been reported for the highly enantioselective rearrangement of indolyl carbonates. Using 2.5 mol% of chiral DMAP-N-oxide, diverse oxindoles containing an all-carbon quaternary stereocenter were obtained in excellent yields (up to 98% yield) with high enantiosel...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2019-12, Vol.6 (23), p.3874-3878
Main Authors: Meng Shan, Liang, Tao, Ye-Fei, Zhang, Ming-Sheng Xie, Gui-Rong Qu, Hai-Ming Guo
Format: Article
Language:English
Subjects:
Carbonates
Catalysts
Enantiomers
N-Oxides
Nitrogen
Organic chemistry
Oxides
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Summary:Bifunctional chiral DMAP-N-oxides have been reported for the highly enantioselective rearrangement of indolyl carbonates. Using 2.5 mol% of chiral DMAP-N-oxide, diverse oxindoles containing an all-carbon quaternary stereocenter were obtained in excellent yields (up to 98% yield) with high enantioselectivities (up to 96% ee). Compared to the widespread use of chiral DMAP and isothiourea catalysts, in which the nitrogen atom serves as a nucleophilic site, we found that chiral DMAP-N-oxides, which utilize the oxygen atom as a nucleophilic site, were also efficient organocatalysts in this rearrangement.
ISSN:2052-4110
2052-4110
DOI:10.1039/c9qo01146c