Chiral Squaramide Catalyzed Asymmetric [3+2] Cycloaddition Reaction for Synthesis of Trifluoromethylated Barbituric Acid Derivatives | Zendy

An TianLi | Zendy; Du DaMing | Zendy

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Chiral Squaramide Catalyzed Asymmetric [3+2] Cycloaddition Reaction for Synthesis of Trifluoromethylated Barbituric Acid Derivatives

Author(s) -

An TianLi,

Du DaMing

Publication year - 2019

Publication title -

chemistryselect

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.437

H-Index - 34

ISSN - 2365-6549

DOI - 10.1002/slct.201903146

Subject(s) - squaramide , stereocenter , chemistry , barbituric acid , isatin , yield (engineering) , stereoselectivity , mannich reaction , catalysis , cycloaddition , enantioselective synthesis , michael reaction , nitroaldol reaction , organocatalysis , organic chemistry , medicinal chemistry , stereochemistry , materials science , metallurgy

A squaramide catalyzed asymmetric Michael/Mannich [3+2] cycloaddition reaction between N ‐2,2,2‐trifluoroethyl isatin ketimines and barbiturate‐based olefins was developed. The corresponding trifluoromethylated dispirobarbituric acid derivatives containing three stereocenters were obtained in excellent yields and stereoselectivities (up to 99% yield, 99:1 dr and >99% ee). In addition, the gram‐scale reaction also achieved with excellent yield and stereoselectivity.

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