Organocatalytic 1,6-hydrophosphination of para-quinone methides: enantioselective access to chiral 3-phosphoxindoles bearing phosphorus-substituted quaternary carbon stereocenters
Literature Information
Publication Date
2021-03-01
DOI
10.1039/D0QO01638A
Impact Factor
5.281
Authors
Fuxing Yang, Xiaoping Xu, Jun Jiang
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
Recommended Compounds
![4-[2-(Trichlorosilyl)ethyl]benzenesulfonyl chloride structure](https://static.chemtradehub.com/structs/797/79793-00-3-de16.webp "4-[2-(Trichlorosilyl)ethyl]benzenesulfonyl chloride structure")
4-[2-(Trichlorosilyl)ethyl]benzenesulfonyl chloride
CAS Number:
79793-00-3
Molecular Formula:
C8H8Cl4O2SSi
3,5-Dihydroxy-4-(3-methylbutanoyl)-2,6,6-tris(3-methyl-2-buten-1-yl)-2,4-cyclohexadien-1-one
CAS Number:
468-28-0
Molecular Formula:
C26H38O4
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