Enantioselective [2 + 2] cycloaddition of 1,2-dihydroquinolines with 3-olefinic oxindoles via Brønsted acid catalysis

文献情報

出版日 2022-02-01

DOI 10.1039/D1QO01708J

インパクトファクター 5.281

著者

Biao Wang, Xiao Yan, Han Zhong, Qin Ouyang, Xu Tian

要旨

Mutually complementary regiodivergent Brønsted acid-catalyzed atom-economical [2 + 2] cycloaddition and ene reactions of 1,2-dihydroquinolines with 3-olefinic oxindoles are reported. In the presence of a chiral phosphoramide catalyst, the [2 + 2] cycloaddition affords products with four contiguous stereocenters in good to excellent yields (up to 95%) and with high stereoselectivities (up to >99% ee, >20 : 1 dr). Conversely, with a stronger Brønsted acid, the trifluoromethanesulfonic acid catalyst leads to ene reaction products in high yields (up to 77%). Furthermore, the mechanisms of the reactions are discussed based on control experiments and DFT calculations.

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