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

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发布日期 2019-10-12

DOI 10.1039/C9QO01146C

影响因子 5.281

作者

Meng Shan, Tao Liang, Ye-Fei Zhang, Ming-Sheng Xie, Gui-Rong Qu, Hai-Ming Guo

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摘要

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.

期刊推荐

Journal of Peptide Science

Russian Chemical Bulletin

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Russian Journal of General Chemistry

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Russian Journal of Organic Chemistry

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Russian Journal of Coordination Chemistry

来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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