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

摘要

Functionalized dialdehydes are considered important substrates, which may be transformed into various substituted heterocycles, 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.