Kinetic resolution of 2H-azirines via Cu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides

文献情報

出版日 2020-09-18

DOI 10.1039/D0QO00789G

インパクトファクター 5.281

著者

Hua Deng, Tian-Tian Liu, Zheng-Dong Ding, Wu-Lin Yang, Xiaoyan Luo

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要旨

A highly efficient kinetic resolution of racemic 2H-azirines has been achieved by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides. With an (S,Sp)-Ph-Phosferrox/Cu(MeCN)4BF4 complex as the catalyst, optically pure 2H-azirines were obtained with excellent enantioselectivities (up to 99% ee) and high resolution efficiency (S factors up to 845). Meanwhile, this process provided a direct approach to synthesize structurally novel 1,3-diazabicyclo[3.1.0]hexane derivatives with excellent enantioselectivities (94–99% ee).

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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

Kinetic resolution of 2H-azirines via Cu(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides

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