Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 10, Pages 5771-5777Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00171
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Funding
- National NSFC [21372217, 21572223, 21572224]
- Sichuan Youth Science and Technology Foundation [2015JQ0041, 2016JQ0024]
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An efficient organocatalyzed enantioselective conjugated addition of sodium bisulfite to beta-trifluoromethyl-alpha,beta-unsaturated ketones using a cinchona alkaloid-derived squaramide catalyst is presented. A series of optically active sulfonic acids, bearing a tertiary stereocenter connecting a CF3 group and a SO3H group, were obtained in excellent yields with high enantioselectivities (up to 99% yield and 97% ee) under mild conditions. This method will provide an efficient, economic, and green route to access chiral sulfonic acid compounds.
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