Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 6, Pages 1292-1300Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201301027
Keywords
asymmetric organocatalysis; oxazolidinone enoates; sulfa-Michael reaction; tertiary thiols; trifluoromethylation
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Funding
- NSFC [21072044, 21202034]
- Excellent Youth Foundation of Henan Scientific Committee [114100510003]
- Specialized Research Fund for the Doctoral Program of Higher Education [20104103120002]
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The first asymmetric conjugate addition of mercaptans to beta-substituted-beta-trifluoromethyl oxazolidinone enoates has been developed. The opposite enantiomers of adducts, containing a trifluoromethylated hetero-quaternary stereogenic centers, could be obtained by utilizing two pseudo-enantiomeric Cinchona alkaloid-derived tertiary amine/squaramides as catalysts. Potassium dihydrogen phosphate was found to accelerate the reaction rate without compromising the enantioselective excess. A variety of chiral trifluoromethylated tertiary thioethers and thiols were readily prepared with excellent enantioselectivity.
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