Premium
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.