Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline

Autores
Kaufman, Teodoro Saul; Amongero, Marcela
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A concise organocatalytic approach towards optically active 1,2,3-trisubstituted azetidines, including a study of the scope and limitations of the synthetic sequence, is reported. The synthesis comprises the one-pot L-proline promoted three-component reaction between substituted benzaldehydes, anilines and enolizable aldehydes, followed by the in situ reduction of the resulting b-aminoaldehydes to the corresponding c-aminoalcohols and final intramolecular cyclization of the latter by way of the intermediate tosylates, formed in situ.
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Amongero, Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Materia
Optically active azetidines
1,2,3-Trisubstituted azetidines
Organocatalysis
Synthesis of nitrogen heterocycles
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/6022
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/6022
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-prolineKaufman, Teodoro SaulAmongero, MarcelaOptically active azetidines1,2,3-Trisubstituted azetidinesOrganocatalysisSynthesis of nitrogen heterocycleshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A concise organocatalytic approach towards optically active 1,2,3-trisubstituted azetidines, including a study of the scope and limitations of the synthetic sequence, is reported. The synthesis comprises the one-pot L-proline promoted three-component reaction between substituted benzaldehydes, anilines and enolizable aldehydes, followed by the in situ reduction of the resulting b-aminoaldehydes to the corresponding c-aminoalcohols and final intramolecular cyclization of the latter by way of the intermediate tosylates, formed in situ.Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Amongero, Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaElsevier2013-01-30info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6022Kaufman, Teodoro Saul; Amongero, Marcela; Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline; Elsevier; Tetrahedron Letters; 54; 15; 30-1-2013; 1924-19270040-4039enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403913001482info:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2013.01.090info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:32:48Zoai:ri.conicet.gov.ar:11336/6022instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:32:48.246CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline
title Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline
spellingShingle Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline
Kaufman, Teodoro Saul
Optically active azetidines
1,2,3-Trisubstituted azetidines
Organocatalysis
Synthesis of nitrogen heterocycles
title_short Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline
title_full Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline
title_fullStr Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline
title_full_unstemmed Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline
title_sort Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline
dc.creator.none.fl_str_mv Kaufman, Teodoro Saul
Amongero, Marcela
author Kaufman, Teodoro Saul
author_facet Kaufman, Teodoro Saul
Amongero, Marcela
author_role author
author2 Amongero, Marcela
author2_role author
dc.subject.none.fl_str_mv Optically active azetidines
1,2,3-Trisubstituted azetidines
Organocatalysis
Synthesis of nitrogen heterocycles
topic Optically active azetidines
1,2,3-Trisubstituted azetidines
Organocatalysis
Synthesis of nitrogen heterocycles
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A concise organocatalytic approach towards optically active 1,2,3-trisubstituted azetidines, including a study of the scope and limitations of the synthetic sequence, is reported. The synthesis comprises the one-pot L-proline promoted three-component reaction between substituted benzaldehydes, anilines and enolizable aldehydes, followed by the in situ reduction of the resulting b-aminoaldehydes to the corresponding c-aminoalcohols and final intramolecular cyclization of the latter by way of the intermediate tosylates, formed in situ.
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Amongero, Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
description A concise organocatalytic approach towards optically active 1,2,3-trisubstituted azetidines, including a study of the scope and limitations of the synthetic sequence, is reported. The synthesis comprises the one-pot L-proline promoted three-component reaction between substituted benzaldehydes, anilines and enolizable aldehydes, followed by the in situ reduction of the resulting b-aminoaldehydes to the corresponding c-aminoalcohols and final intramolecular cyclization of the latter by way of the intermediate tosylates, formed in situ.
publishDate 2013
dc.date.none.fl_str_mv 2013-01-30
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/6022
Kaufman, Teodoro Saul; Amongero, Marcela; Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline; Elsevier; Tetrahedron Letters; 54; 15; 30-1-2013; 1924-1927
0040-4039
url http://hdl.handle.net/11336/6022
identifier_str_mv Kaufman, Teodoro Saul; Amongero, Marcela; Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline; Elsevier; Tetrahedron Letters; 54; 15; 30-1-2013; 1924-1927
0040-4039
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403913001482
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2013.01.090
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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