Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis† †Electronic supplementary information (ESI) available: Experimental details including characterization date, copies of 1H, 13C, and 19F NMR and HPLC traces. See DOI: 10.1039/c6sc03109a Click here for additional data file.

Abstract

A reagent-controlled enantioselectivity switch was uncovered in the asymmetric a-fluorination of bketocarbonyls 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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Cite this paper

@inproceedings{You2017ReagentcontrolledES, title={Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis† †Electronic supplementary information (ESI) available: Experimental details including characterization date, copies of 1H, 13C, and 19F NMR and HPLC traces. See DOI: 10.1039/c6sc03109a Click here for additional data file. }, author={Yang'en You and Long Yun Zhang and Sanzhong Luo}, year={2017} }