Journal
CHEMICAL SCIENCE
Volume 8, Issue 1, Pages 621-626Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6sc03109a
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Funding
- Ministry of Science and Technology [2012CB821600]
- Natural Science Foundation of China
- Chinese Academy of Sciences
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A reagent-controlled enantioselectivity switch was uncovered in the asymmetric alpha-fluorination of beta-ketocarbonyls by a chiral primary amine catalyst. By a simple swap of fluorination reagents, both enantiomers of the quaternary fluorination adducts could be obtained with good yields and high enantioselectivity. Mechanistic studies disclosed dual H-bonding and electrostatic stereocontrolling modes for the catalysis.
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