TY - JOUR A1 - Kiss, Loránd A1 - Nonn, Melinda A1 - Sillanpää, Reijo A1 - Fustero, Santos A1 - Fülöp, Ferenc T1 - Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates JF - Beilstein Journal of Organic Chemistry PY - 2013/// VL - 9 SP - 1164 EP - 1169 SN - 1860-5397 DO - 10.3762/bjoc.9.130 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.9.130 KW - amino acids KW - epoxidation KW - fluorination KW - hydroxylation KW - stereoselective reaction N2 - 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. ER -