Organocatalytic 1,6-hydrophosphination of para-quinone methides: enantioselective access to chiral 3-phosphoxindoles bearing phosphorus-substituted quaternary carbon stereocenters

文献情報

出版日 2021-03-01

DOI 10.1039/D0QO01638A

インパクトファクター 5.281

著者

Fuxing Yang, Xiaoping Xu, Jun Jiang

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要旨

An efficient organocatalytic enantioselective 1,6-hydrophosphonylation of para-quinone methides derived from isatins with H-phosphorus oxides has been achieved in the presence of bifunctional cinchona alkaloid-based urea. This methodology provides a straightforward approach for accessing a variety of chiral 3-phosphoxindoles bearing phosphorus-substituted quaternary carbon stereocenters with a high level of chemoselectivity and remote stereocontrol (up to 99% yield, 99 : 1 er). This environmentally benign protocol represents a unique example of the asymmetric organocatalytic 1,6-conjugate addition reaction of phosphorus nucleophiles in an atom-economical manner.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 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

Organocatalytic 1,6-hydrophosphination of para-quinone methides: enantioselective access to chiral 3-phosphoxindoles bearing phosphorus-substituted quaternary carbon stereocenters

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