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

doi:10.1016/j.tet.2011.08.079

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

Chemistry

Charles University
Universitat de Barcelona

Research output: Contribution to journal › Article › peer-review

43 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 language	British English
Pages (from-to)	8942-8950
Number of pages	9
Journal	Tetrahedron
Volume	67
Issue number	46
DOIs	https://doi.org/10.1016/j.tet.2011.08.079
State	Published - 18 Nov 2011

Keywords

Cascade reaction
Diastereoselective
Enantioselective
Organocatalysis
Paroxetine

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10.1016/j.tet.2011.08.079

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@article{9798f3a6cab746c885bc8c6626471981,

title = "Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines",

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.",

keywords = "Cascade reaction, Diastereoselective, Enantioselective, Organocatalysis, Paroxetine",

author = "Sylva {\v C}{\'i}halov{\'a} and Guillem Valero and Ji{\v r}{\'i} Schimer and Marek Humpl and Martin Dra{\v c}{\'i}nsk{\'y} and Albert Moyano and Ramon Rios and Jan Vesely",

note = "Funding Information: J.V. gratefully acknowledges the Grant Agency of Czech Republic ( GACR 203/09/P193 ) and Ministry of Education, Youth and Sport (No. MSM0021620857 ), R.R. and A.M. thank to Spanish Ministry of Science and Innovation (MICINN) for financial support (Project AYA2009-13920-C02-02). G.V. is also grateful to MICINN for his pre-doctoral fellowship. J.V. also thanks to Dr. C{\'i}sa{\v r}ov{\'a} for X-ray studies.",

year = "2011",

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doi = "10.1016/j.tet.2011.08.079",

language = "British English",

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TY - JOUR

T1 - Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines

AU - Číhalová, Sylva

AU - Valero, Guillem

AU - Schimer, Jiří

AU - Humpl, Marek

AU - Dračínský, Martin

AU - Moyano, Albert

AU - Rios, Ramon

AU - Vesely, Jan

N1 - Funding Information: J.V. gratefully acknowledges the Grant Agency of Czech Republic ( GACR 203/09/P193 ) and Ministry of Education, Youth and Sport (No. MSM0021620857 ), R.R. and A.M. thank to Spanish Ministry of Science and Innovation (MICINN) for financial support (Project AYA2009-13920-C02-02). G.V. is also grateful to MICINN for his pre-doctoral fellowship. J.V. also thanks to Dr. Císařová for X-ray studies.

PY - 2011/11/18

Y1 - 2011/11/18

N2 - 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.

AB - 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.

KW - Cascade reaction

KW - Diastereoselective

KW - Enantioselective

KW - Organocatalysis

KW - Paroxetine

UR - https://www.scopus.com/pages/publications/80054006801

U2 - 10.1016/j.tet.2011.08.079

DO - 10.1016/j.tet.2011.08.079

M3 - Article

AN - SCOPUS:80054006801

SN - 0040-4020

VL - 67

SP - 8942

EP - 8950

JO - Tetrahedron

JF - Tetrahedron

IS - 46

ER -

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

Abstract

Keywords

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