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

Kiss, Loránd and Nonn, Melinda and Sillanpaa, Reijo and Fustero, Santos and Fülöp, Ferenc (2013) Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates. Beilstein Journal of Organic Chemistry, 9. pp. 1164-1169. ISSN ESSN: 1860-5397

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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-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.

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