Design and Synthesis of Novel C2-symmetric bis-cinchona Alkaloid Derivatives

Title:Design and Synthesis of Novel C2-symmetric bis-cinchona Alkaloid Derivatives

Volume: 13 Issue: 6

Author(s): MingKun Qin, MingXiang Gao, JiangTao Li, ZhiYong Jiang and Lin Yan

Affiliation:

Keywords: Brønsted acid, catalyst, Cinchona alkaloids, C2-symmetric, synthesis.

Abstract: Background: The commercially available dimeric cinchona alkaloids based on C-9 ether bond connecting are limited by the absence of Brønsted acid moiety and cannot meet the enantioselectivity demand.

Objective: In this study, a family of novel C2-symmetric bis-cinchona alkaloid derivatives possessing a range of mono- and bidentate hydrogen bond donor groups at the C-9 is now reported. Method: These novel C2-symmetric bis-cinchona alkaloid derivatives were synthesized by a facile route.

Results: These novel C2-symmetric bis-cinchona alkaloid derivatives exhibit a rare example of Brønsted acid moiety of C-9, basic tertiary amine moiety, and a rigid enzyme-like pocket, suggesting their potential, broadly useful bifunctional organic catalysts for asymmetric synthesis.

Cite this article as:

Qin MingKun, Gao MingXiang, Li JiangTao, Jiang ZhiYong and Yan Lin, Design and Synthesis of Novel C2-symmetric bis-cinchona Alkaloid Derivatives, Letters in Organic Chemistry 2016; 13 (6) . https://dx.doi.org/10.2174/1570178613666160815094631