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Efficient regio- and stereoselective access to novel fluorinated ?-aminocyclohexanecarboxylates.

ABSTRACT: A regio- and stereoselective method has been developed for the synthesis of novel fluorinated 2-aminocyclohexanecarboxylic acid derivatives with the fluorine attached to position 4 of the ring. The synthesis starts from either cis- or trans-?-aminocyclohex-4-enecarboxylic acids and involves regio- and stereoselective transformation of the ring C-C double bond through iodooxazine formation and hydroxylation, followed by hydroxy-fluorine or oxo-fluorine exchange.

SUBMITTER: Kiss L

PROVIDER: S-EPMC3701410 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates.

Kiss Loránd L Nonn Melinda M Sillanpää Reijo R Fustero Santos S Fülöp Ferenc F

Beilstein journal of organic chemistry 20130617

A regio- and stereoselective method has been developed for the synthesis of novel fluorinated 2-aminocyclohexanecarboxylic acid derivatives with the fluorine attached to position 4 of the ring. The synthesis starts from either cis- or trans-β-aminocyclohex-4-enecarboxylic acids and involves regio- and stereoselective transformation of the ring C-C double bond through iodooxazine formation and hydroxylation, followed by hydroxy-fluorine or oxo-fluorine exchange. ...[more]

PMID: 23843909

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