6533b7dafe1ef96bd126ea7b

RESEARCH PRODUCT

Functionalized Dialdehydes as Promising Scaffolds for Access to Heterocycles and β-Amino Acids: Synthesis of Fluorinated Piperidine and Azepane Derivatives

Santos FusteroLoránd KissFerenc FülöpFerenc FülöpRenata Anita Abrahami

subject

chemistry.chemical_classification010405 organic chemistryOrganic ChemistryAlkylation010402 general chemistryRing (chemistry)Cleavage (embryo)01 natural sciencesCatalysis0104 chemical sciencesAmino acidchemistry.chemical_compoundAlicyclic compoundchemistryAzepaneBioorganic chemistryOrganic chemistryPiperidine

description

Functionalized dialdehydes are considered important substrates that can be transformed into various substituted heterocyclic, alicyclic, and polysubstituted compounds. Here, we report a robust stereocontrolled procedure for the synthesis of novel functionalized trifluoromethyl-containing piperidine and azepane derivatives, based on oxidative ring cleavage of the C=C bond of diversely substituted cycloalkenes, followed by reductive ring closure of the diformyl intermediates in the presence of fluorine-containing amines.

https://doi.org/10.1055/s-0036-1588396