Asymmetric organocatalytic conjugated addition of pyrazolin-5-ones to ortho-quinomethanes: construction of vicinal tertiary and all-carbon quaternary stereocenters

Literature Information

Publication Date 2019-02-27
DOI 10.1039/C9QO00011A
Impact Factor 5.281
Authors

Ming-Ming Chu, Suo-Suo Qi, Wan-Zhen Ju, Yi-Feng Wang, Xue-Yang Chen, Dan-Qian Xu, Zhen-Yuan Xu


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Abstract

A chiral amine squaramide catalyzed the conjugated addition of pyrazolin-5-ones to in situ generated ortho-quinomethanes (o-QMs) was developed to construct 4-tetrasubstituted pyrazolin-5-ones featuring adjacent quaternary and tertiary stereocenters in oil–water phases. High yields, excellent stereoselectivities, mild conditions and accessible scale-up demonstrated the fascination of this reaction protocol.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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