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

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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

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* 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

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DOI: https://doi.org/10.1039/C7RA08157J
Article type: Paper
Submitted: 24 7月 2017
Accepted: 25 7月 2017
First published: 10 8月 2017
This article is Open Access

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RSC Adv., 2017,7, 39216-39220

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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

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

Abstract

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

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