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

Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines
Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines
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.
organocatalysis, paroxetine, enantioselective, cascade reaction, diastereoselective
0040-4020
8942-8950
Číhalová, Sylva
450f3eb8-530d-4a73-a9bd-76858defcd7b
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Schimer, Jiří
41f67827-5ffd-4b7d-9ac8-a289036427ac
Humpl, Marek
c29b002d-b190-4107-991d-35e677b5bc36
Dračínský, Martin
0950c4a0-b4e7-43fd-a1b3-cede949b5ce8
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Číhalová, Sylva
450f3eb8-530d-4a73-a9bd-76858defcd7b
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Schimer, Jiří
41f67827-5ffd-4b7d-9ac8-a289036427ac
Humpl, Marek
c29b002d-b190-4107-991d-35e677b5bc36
Dračínský, Martin
0950c4a0-b4e7-43fd-a1b3-cede949b5ce8
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3

Číhalová, Sylva, Valero, Guillem, Schimer, Jiří, Humpl, Marek, Dračínský, Martin, Moyano, Albert, Rios, Ramon and Vesely, Jan (2011) Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines. Tetrahedron, 67 (46), 8942-8950. (doi:10.1016/j.tet.2011.08.079).

Record type: Article

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.

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Published date: 18 November 2011
Keywords: organocatalysis, paroxetine, enantioselective, cascade reaction, diastereoselective
Organisations: Chemistry

Identifiers

Local EPrints ID: 347687
URI: http://eprints.soton.ac.uk/id/eprint/347687
ISSN: 0040-4020
PURE UUID: 2569ba24-d240-4650-b5e7-cfe44348aa18
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 10:12
Last modified: 10 Dec 2019 01:37

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Contributors

Author: Sylva Číhalová
Author: Guillem Valero
Author: Jiří Schimer
Author: Marek Humpl
Author: Martin Dračínský
Author: Albert Moyano
Author: Ramon Rios ORCID iD
Author: Jan Vesely

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