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

Lili Zhang; Xiao Zhou; Pengfei Li; Zhantao Liu; Yang Liu; Yong Sun; Wenjun Li

doi:10.1039/C7RA08157J

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Lili Zhang,‡^a Xiao Zhou,‡^a Pengfei Li,^b Zhantao Liu,^a Yang Liu,^a Yong Sun^a and Wenjun Li

*^a

Author affiliations

* Corresponding authors

^a Department of Medicinal Chemistry, School of Pharmacy, Qingdao University, Qingdao, China
E-mail: liwj@qdu.edu.cn

^b Department of Chemistry, South University of Science and Technology of China, Shenzhen, China

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.

This article is part of the themed collections: Asymmetric catalysis and Editors’ collection: Catalytic Organic Transformations

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C7RA08157J
Article type: Paper
Submitted: 24 Jul 2017
Accepted: 25 Jul 2017
First published: 10 Aug 2017
This article is Open Access

Download Citation

RSC Adv., 2017,7, 39216-39220

Permissions

Request permissions

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.

Social activity

Fetching data from CrossRef.
This may take some time to load.

RSC Advances

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements