The facile and stereoselective synthesis of pyrrolidine β-amino acids via copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition

文献情報

出版日 2016-10-08

DOI 10.1039/C6QO00512H

インパクトファクター 5.281

著者

Fu-Sheng He, Cong-Shan Li, Hua Deng, Xing Zheng, Zhong-Tao Yang, Wei-Ping Deng

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要旨

A highly efficient copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with β-phthaliminoacrylate esters was developed under mild conditions, providing the desired pyrrolidine β-amino acid derivatives in high yields (up to 98%) with excellent diastereo- and enantioselectivities (dr >20 : 1, ee up to >99%). Subsequent deprotection and hydrogenolysis of the corresponding cycloadducts could deliver highly functionalized and biologically important free pyrrolidine β-amino acids in a straightforward and efficient pathway.

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

The facile and stereoselective synthesis of pyrrolidine β-amino acids via copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition

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