Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 6, Pages 1141-1147Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100899
Keywords
amine-thiourea catalysts; asymmetric center dot catalysis; pyrazoles; sulfa-Michael addition; 4; 4; 4-trifluorocrotonamide; trifluoromethyl group
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Funding
- National Natural Science Foundation of China [20972117, 21172176]
- Program for New Century Excellent Talents in University [NCET-10-0649]
- Ministry of Education [IRT1030]
- 973 program [2011CB808600]
- Fundamental Research Funds for the Central Universities
- Large-scale Instrument And Equipment Sharing Foundation of Wuhan University
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A new protocol for the efficient construction of chiral trifluoromethylated building blocks was developed via organocatalyzed sulfa-Michael addition of thiols to the cost-efficient trans-trifluorocrotonamide. Introducing the pyrazole moiety is crucial to providing H-bond acceptor sites for better activation and hence affording comparable asymmetric induction with that obtained when employing the expensive cis-4,4,4-trifluorocrotonate as the Michael acceptor.
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