Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides

Autores
Gerbino, Darío César; Scoccia, Jimena; Koll, Liliana Cristina; Mandolesi, Sandra Delia; Podestá, Julio Cesar
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Radical tandem addition of dialkyltin chlorohydrides, R2SnHCl (R = n-Bu, neophyl, Ph), to TADDOL's substituted diacrylates (47) led to the corresponding products of cyclohydrostannation. The new optically active chlorodialkyltinsubstituted 11-membered macrodiolides were obtained in very good yields and with much higher stereoselectivity than that achieved with the corresponding monohydrides, R3SnH. Thus, the cyclohydrostannation of diacrylate 4 and dimethacrylate 5 lead to just one diastereomer in the first case and to an easily separable mixture of two diastereomers in the second. Reduction of the new organotin macrocycles with LiAlH4 afforded optically active organotin derivatives structurally related to glutaric acid. Oxidation of the new chlorodiorganotin-substituted macrocycles with 30% hydrogen peroxide gave the new 11-membered macrocycles 30 and 31 free of tin in an average total yield of 43.4% from TADDOL. Full 1H, 13C, and 119Sn data are also reported. © 2012 American Chemical Society.
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Scoccia, Jimena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Mandolesi, Sandra Delia. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Materia
Taddol
Macrodiolides
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/64660
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolidesGerbino, Darío CésarScoccia, JimenaKoll, Liliana CristinaMandolesi, Sandra DeliaPodestá, Julio CesarTaddolMacrodiolideshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Radical tandem addition of dialkyltin chlorohydrides, R2SnHCl (R = n-Bu, neophyl, Ph), to TADDOL's substituted diacrylates (47) led to the corresponding products of cyclohydrostannation. The new optically active chlorodialkyltinsubstituted 11-membered macrodiolides were obtained in very good yields and with much higher stereoselectivity than that achieved with the corresponding monohydrides, R3SnH. Thus, the cyclohydrostannation of diacrylate 4 and dimethacrylate 5 lead to just one diastereomer in the first case and to an easily separable mixture of two diastereomers in the second. Reduction of the new organotin macrocycles with LiAlH4 afforded optically active organotin derivatives structurally related to glutaric acid. Oxidation of the new chlorodiorganotin-substituted macrocycles with 30% hydrogen peroxide gave the new 11-membered macrocycles 30 and 31 free of tin in an average total yield of 43.4% from TADDOL. Full 1H, 13C, and 119Sn data are also reported. © 2012 American Chemical Society.Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Scoccia, Jimena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Mandolesi, Sandra Delia. Universidad Nacional del Sur. Departamento de Química; ArgentinaFil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaAmerican Chemical Society2012-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/64660Gerbino, Darío César; Scoccia, Jimena; Koll, Liliana Cristina; Mandolesi, Sandra Delia; Podestá, Julio Cesar; Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides; American Chemical Society; Organometallics; 31; 2; 1-2012; 662-6710276-7333CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/om200987tinfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/om200987tinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:17:00Zoai:ri.conicet.gov.ar:11336/64660instacron: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:34982025-09-10 13:17:01.13CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides
title Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides
spellingShingle Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides
Gerbino, Darío César
Taddol
Macrodiolides
title_short Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides
title_full Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides
title_fullStr Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides
title_full_unstemmed Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides
title_sort Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides
dc.creator.none.fl_str_mv Gerbino, Darío César
Scoccia, Jimena
Koll, Liliana Cristina
Mandolesi, Sandra Delia
Podestá, Julio Cesar
author Gerbino, Darío César
author_facet Gerbino, Darío César
Scoccia, Jimena
Koll, Liliana Cristina
Mandolesi, Sandra Delia
Podestá, Julio Cesar
author_role author
author2 Scoccia, Jimena
Koll, Liliana Cristina
Mandolesi, Sandra Delia
Podestá, Julio Cesar
author2_role author
author
author
author
dc.subject.none.fl_str_mv Taddol
Macrodiolides
topic Taddol
Macrodiolides
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Radical tandem addition of dialkyltin chlorohydrides, R2SnHCl (R = n-Bu, neophyl, Ph), to TADDOL's substituted diacrylates (47) led to the corresponding products of cyclohydrostannation. The new optically active chlorodialkyltinsubstituted 11-membered macrodiolides were obtained in very good yields and with much higher stereoselectivity than that achieved with the corresponding monohydrides, R3SnH. Thus, the cyclohydrostannation of diacrylate 4 and dimethacrylate 5 lead to just one diastereomer in the first case and to an easily separable mixture of two diastereomers in the second. Reduction of the new organotin macrocycles with LiAlH4 afforded optically active organotin derivatives structurally related to glutaric acid. Oxidation of the new chlorodiorganotin-substituted macrocycles with 30% hydrogen peroxide gave the new 11-membered macrocycles 30 and 31 free of tin in an average total yield of 43.4% from TADDOL. Full 1H, 13C, and 119Sn data are also reported. © 2012 American Chemical Society.
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Scoccia, Jimena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Koll, Liliana Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Mandolesi, Sandra Delia. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
description Radical tandem addition of dialkyltin chlorohydrides, R2SnHCl (R = n-Bu, neophyl, Ph), to TADDOL's substituted diacrylates (47) led to the corresponding products of cyclohydrostannation. The new optically active chlorodialkyltinsubstituted 11-membered macrodiolides were obtained in very good yields and with much higher stereoselectivity than that achieved with the corresponding monohydrides, R3SnH. Thus, the cyclohydrostannation of diacrylate 4 and dimethacrylate 5 lead to just one diastereomer in the first case and to an easily separable mixture of two diastereomers in the second. Reduction of the new organotin macrocycles with LiAlH4 afforded optically active organotin derivatives structurally related to glutaric acid. Oxidation of the new chlorodiorganotin-substituted macrocycles with 30% hydrogen peroxide gave the new 11-membered macrocycles 30 and 31 free of tin in an average total yield of 43.4% from TADDOL. Full 1H, 13C, and 119Sn data are also reported. © 2012 American Chemical Society.
publishDate 2012
dc.date.none.fl_str_mv 2012-01
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/11336/64660
Gerbino, Darío César; Scoccia, Jimena; Koll, Liliana Cristina; Mandolesi, Sandra Delia; Podestá, Julio Cesar; Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides; American Chemical Society; Organometallics; 31; 2; 1-2012; 662-671
0276-7333
CONICET Digital
CONICET
url http://hdl.handle.net/11336/64660
identifier_str_mv Gerbino, Darío César; Scoccia, Jimena; Koll, Liliana Cristina; Mandolesi, Sandra Delia; Podestá, Julio Cesar; Stereoselective synthesis and some properties of new chlorodiorganotin- substituted macrodiolides; American Chemical Society; Organometallics; 31; 2; 1-2012; 662-671
0276-7333
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/om200987t
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/om200987t
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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 12.993085

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