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Reagent-controlled enantioselectivity switch for the asymmetric fluorination of ?-ketocarbonyls by chiral primary amine catalysis.

ABSTRACT: A reagent-controlled enantioselectivity switch was uncovered in the asymmetric ?-fluorination of ?-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.

SUBMITTER: You Y

PROVIDER: S-EPMC5358536 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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Reagent-controlled enantioselectivity switch for the asymmetric fluorination of β-ketocarbonyls by chiral primary amine catalysis.

You Yang'en Y Zhang Long L Luo Sanzhong S

Chemical science 20160826 1

A reagent-controlled enantioselectivity switch was uncovered in the asymmetric α-fluorination of β-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. ...[more]

PMID: 28451209

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