Issue 35, 2018

Asymmetric synthesis of warfarin and its analogs catalyzed by C2-symmetric squaramide-based primary diamines

Abstract

Novel C2-symmetric N,N′-bis(2-amino-1,2-diphenylethyl)squaramides with 1,2-di(pyridin-2-yl)ethane and 1,2-diphenylethane spacer groups were designed and applied as organocatalysts in asymmetric additions of 4-hydroxycoumarin and 4-hydroxy-6-methyl-2H-pyran-2-one to α,β-unsaturated ketones. Both enantiomers of the anticoagulant warfarin and its analogs were prepared in up to 96% yield and with 96% ee. Recyclability of the developed catalysts and synthetic utility of the prepared Michael adducts for asymmetric synthesis of potential chiral medications via acylation reactions were demonstrated.

Graphical abstract: Asymmetric synthesis of warfarin and its analogs catalyzed by C2-symmetric squaramide-based primary diamines

Supplementary files

Article information

Article type
Paper
Submitted
04 Jul 2018
Accepted
24 Jul 2018
First published
24 Jul 2018

Org. Biomol. Chem., 2018,16, 6423-6429

Asymmetric synthesis of warfarin and its analogs catalyzed by C2-symmetric squaramide-based primary diamines

S. V. Kochetkov, A. S. Kucherenko and S. G. Zlotin, Org. Biomol. Chem., 2018, 16, 6423 DOI: 10.1039/C8OB01576G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements