Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates
نویسندگان
چکیده
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.
منابع مشابه
Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel α-fluoroenamides.
α-Fluoroenamides, potent rigid fluorinated bioisosters of ureas, have been synthesized by a highly regio- and stereo-selective hydrofluorination of ynamides in anhydrous HF. This reaction provides the first general entry to α-fluoroenamides and can easily be applied to a wide range of substrates.
متن کاملRegio- and diastereoselective nickel-catalyzed allylation of aromatic aldehydes with α-halo-β,β-difluoropropene derivatives.
A one-pot nickel-catalyzed allylation of aromatic aldehydes with α-halo-β,β-difluoropropene-containing compounds promoted by ZnEt(2) under mild conditions was described. The reaction displays moderate to good regio- and diastereoselectivity, tolerates a wide range of functional groups, and provides an efficient method for the synthesis of γ-fluorinated homoallylic alcohols.
متن کاملRegio- and stereoselective synthesis of 2-cyclopentenones via a hydrogenolysis-terminated Heck cyclization of β-alkylthio dienones.
Palladium-catalyzed cyclization of β-alkylthio dienone derivatives affords 2-cyclopentenones in a regio- and stereoselective manner in the presence of silane. C-S activation, intramolecular carbopalladation and hydrogenolysis construct the cascade process.
متن کاملRegio- and stereoselective copper-catalyzed β-borylation of allenoates by a preactivated diboron.
A mild and efficient copper-catalyzed borylation of electron deficient allenoates using an sp(2)-sp(3) mixed hybridized diboron regioselectively installs a boron moiety on the β-position with exclusive (Z)-double bond geometry.
متن کاملMetallophthalocyanine complex, Cr(TBPC)OTf: an efficient, recyclable Lewis acid catalyst in the regio- and stereoselective rearrangement of epoxides to aldehydes.
The metallophthalocyanine complex Cr(TBPC)OTf works as a highly efficient, recyclable Lewis acid catalyst for the regio- and stereoselective rearrangements of epoxides to aldehydes.
متن کامل