Synthesis 2017; 49(06): 1206-1213
DOI: 10.1055/s-0036-1588396
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© Georg Thieme Verlag Stuttgart · New York

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

Renáta A. Ábrahámi
a  Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary   Email: fulop@pharm.u-szeged.hu
,
Loránd Kiss
a  Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary   Email: fulop@pharm.u-szeged.hu
,
Santos Fustero
c  Departamento de Química Orgánica, Facultad de Farmácia, Universidad de Valencia, Av. Vincente Andrés Estellés, s/n 461000 Valencia, Spain
,
Ferenc Fülöp*
a  Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary   Email: fulop@pharm.u-szeged.hu
b  MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, 6720 Szeged, Eötvös u. 6, Hungary
› Author Affiliations
Further Information

Publication History

Received: 19 December 2016

Accepted: 23 December 2016

Publication Date:
24 January 2017 (online)


Abstract

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.

Supporting Information

 
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