Issue 62, 2017

Asymmetric synthesis of chromene skeletons via organocatalytic domino reactions of in situ generated ortho-quinone methide with malononitrile and β-functionalized ketone

Abstract

Enantioselective organocatalytic domino reactions of in situ generated ortho-quinone methides with malononitrile and β-functionalized ketones have been developed. This strategy could generate various chiral chromenes in high yields (up to 99%) and stereoselectivities (up to >99 : 1 e.r.) in the presence of 5 mol% of a bifunctional organocatalyst. Gram-scale and useful synthetic transformations of this process are also presented.

Graphical abstract: Asymmetric synthesis of chromene skeletons via organocatalytic domino reactions of in situ generated ortho-quinone methide with malononitrile and β-functionalized ketone

Supplementary files

Article information

Article type
Paper
Submitted
24 Jūl. 2017
Accepted
25 Jūl. 2017
First published
10 Aug. 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 39216-39220

Asymmetric synthesis of chromene skeletons via organocatalytic domino reactions of in situ generated ortho-quinone methide with malononitrile and β-functionalized ketone

L. Zhang, X. Zhou, P. Li, Z. Liu, Y. Liu, Y. Sun and W. Li, RSC Adv., 2017, 7, 39216 DOI: 10.1039/C7RA08157J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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