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

Renáta A. Ábrahámi, L. Kiss, Santos Fustero, F. Fülöp

Research output: Contribution to journalArticle

7 Citations (Scopus)

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.

Original languageEnglish
Article numberss-2016-z0870-fa
Pages (from-to)1206-1213
Number of pages8
JournalSynthesis (Germany)
Volume49
Issue number6
DOIs
Publication statusPublished - Mar 15 2017

Fingerprint

Cycloparaffins
Fluorine
Scaffolds
Amines
Amino acids
Derivatives
Amino Acids
Substrates
piperidine

Keywords

  • aldehydes
  • alkylation
  • amino acids
  • bioorganic chemistry
  • expansion
  • heterocycles
  • piperidines

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Functionalized Dialdehydes as Promising Scaffolds for Access to Heterocycles and β-Amino Acids : Synthesis of Fluorinated Piperidine and Azepane Derivatives. / Ábrahámi, Renáta A.; Kiss, L.; Fustero, Santos; Fülöp, F.

In: Synthesis (Germany), Vol. 49, No. 6, ss-2016-z0870-fa, 15.03.2017, p. 1206-1213.

Research output: Contribution to journalArticle

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