Pyridine-N-oxide catalyzed acylative desymmetrization of bisphenols: access to P-stereogenic phosphinates with low catalyst loadings

Literature Information

Publication Date 2023-10-31
DOI 10.1039/D3QO01499A
Impact Factor 5.281
Authors

Yang-Guang Chen, Ying Hu, Jia-Yi Liu, Ming-Sheng Xie


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Abstract

A catalytic stereoselective strategy to access P-stereogenic phosphinates through chiral 4-arylpyridine-N-oxide-catalyzed acylative desymmetrization of bisphenols has been reported. In the presence of 0.05 mol% 4-arylpyridine-N-oxide catalyst, chiral P-stereogenic phosphinates were obtained in up to 97% yields and 96% ee under mild conditions for 2 h. A series of chiral phosphorus compounds containing carboxylic acid drug molecules such as gemfibrozil, isoxepac, and indomethacin were synthesized with high yields and high enantioselectivities.

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Source Journal

Organic Chemistry Frontiers

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

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