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

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

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 6 , 2016

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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.

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

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Article Details

VOLUME: 13
ISSUE: 6
Year: 2016
Page: [446 - 449]
Pages: 4
DOI: 10.2174/1570178613666160815094631
Price: $58

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