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How cinchona alkaloid-derived primary amines control asymmetric electrophilic fluorination of cyclic ketones.

ABSTRACT: The origin of selectivity in the ?-fluorination of cyclic ketones catalyzed by cinchona alkaloid-derived primary amines is determined with density functional calculations. The chair preference of a seven-membered ring at the fluorine transfer transition state is key in determining the sense and level of enantiofacial selectivity.

SUBMITTER: Lam YH

PROVIDER: S-EPMC4105079 | biostudies-other | 2014 Jul

REPOSITORIES: biostudies-other

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How cinchona alkaloid-derived primary amines control asymmetric electrophilic fluorination of cyclic ketones.

Lam Yu-hong YH Houk K N KN

Journal of the American Chemical Society 20140626 27

The origin of selectivity in the α-fluorination of cyclic ketones catalyzed by cinchona alkaloid-derived primary amines is determined with density functional calculations. The chair preference of a seven-membered ring at the fluorine transfer transition state is key in determining the sense and level of enantiofacial selectivity. ...[more]

PMID: 24967514

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