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

Abrahami, Renata Anita and Kiss, Loránd and Fustero, Santos and Fülöp, Ferenc (2017) Functionalized Dialdehydes as Promising Scaffolds for Access to Heterocycles and beta-Amino Acids: Synthesis of Fluorinated Piperidine and Azepane Derivatives. Synthesis-Stuttgart, 49. pp. 1206-1213. ISSN 0039-7881

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Abstract

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.

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