Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines

Sylva Číhalová, Guillem Valero, Jiří Schimer, Marek Humpl, Martin Dračínský, Albert Moyano, Ramon Rios, Jan Vesely

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

Abstract

The synthesis of piperidines and piperidines derivatives in enantiopure fashion has been a challenging goal for organic chemists. In this report we developed a nice cascade reaction for piperidine derivatives based in an amidomalonate Michael addition to enals followed by an intramolecular hemiaminal formation with good yields and enantioselectivities. Moreover we studied the 'in situ' intramolecular cyclization of this hemiaminals with alcohols forming fused piperidine-oxazolidines.

Original languageBritish English
Pages (from-to)8942-8950
Number of pages9
JournalTetrahedron
Volume67
Issue number46
DOIs
StatePublished - 18 Nov 2011

Keywords

  • Cascade reaction
  • Diastereoselective
  • Enantioselective
  • Organocatalysis
  • Paroxetine

Fingerprint

Dive into the research topics of 'Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines'. Together they form a unique fingerprint.

Cite this