Stereoselective synthesis of Δ(1)-pyrroline sulfonamides via a chiral aldehyde mediated cascade reaction

文献情報

出版日 2023-11-15

DOI 10.1039/D3QO01675G

インパクトファクター 5.281

著者

Wei Wen, Zhao-Pin Ai, Zhu-Lian Wu, Tian Cai, Qi-Xiang Guo

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要旨

Functionalized chiral heterocycles play important roles in drug discovery and development. Cascade reactions are powerful strategies for the construction of structurally complex chiral heterocycles. Herein, a catalytic asymmetric Michael addition/spiroannulation/ring cleavage cascade reaction between NH2-free glycinate and cyclic 1-azadienes is established by using a novel chiral aldehyde catalyst, which results in the formation of optically active Δ(1)-pyrroline sulfonamides with high efficiency and high diastereo- and enantioselectivities. Notably, the use of the newly developed chiral aldehyde catalyst led to not only an enhanced reaction rate but also reversed chiral induction compared with its analogue bearing the same configurations.

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

Stereoselective synthesis of Δ(1)-pyrroline sulfonamides via a chiral aldehyde mediated cascade reaction

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