Asymmetric organocatalysis involving double activation

Tetrahedron Chem

Ying-Chun Chen¹  Wei Du²  Zhi Chen²  Qian-Qian Yang³ 

[1] Corresponding author.;Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041, China;State Key Laboratory of Southwestern Chinese Medicine Resources, Hospital of Chengdu University of Traditional Chinese Medicine, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, 611137, China;

关键词: Organocatalysis;    Double activation;    Lewis base catalysis;    Brønsted acid catalysis;    Brønsted base catalysis;    Enantioselectivity;   

DOI  :  

来源: DOAJ

【 摘 要 】

Asymmetric organocatalysis contributed tremendously to the field of organic synthesis since year 2000. Considering the diversity of organocatalysts and their activation modes, chemists developed the double activation strategy, in which two distinct catalysts simultaneously interact with a single substrate, thus enabling effective transformations that might be too challenging or even unattainable under a sole catalytic system. This review summarized the asymmetric reactions via double activation catalysis involving different Lewis bases (aminocatalysts, N-heterocyclic carbenes, isothioureas, N,N-dimethyl-4-aminopyridine, tertiary amines/phosphines, or even thiols), Brønsted bases (including phase transfer catalysts), Brønsted acids, and a few examples combining organocatalysts and metal catalysts or photocatalysts were also discussed. In most cases, compared to those with a single catalyst, better reactivity and stereoselectivity, or even completely different regioselectivity or chemoselectivity were observed under double activation catalysis, demonstrating the power and superiority of this promising strategy. Some key intermediates as well as the mechanisms have been presented to provide insights into the activation processes, which might inspire the development of new double activation systems and more interesting work in the future.

【 授权许可】

Unknown