Synthesis of organotin derivatives of optically active eleven-membered macrodiolides

Autores
Scoccia, Jimena; Gerbino, Darío César; Podestá, Julio Cesar
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis and the results obtained in the hydrostannation of eight new TADDOL diacrylates and methacrylates are reported. The addition of triorganotin hydrides, R3SnH, 12-14 (R = nBu, neophyl, Ph, respectively) to diesters 6-11 containing different combinations of substituents at the C-2 carbon of the dioxolane ring, led to macrocyclization products in all cases. The cyclohydrostannation of diacrylate 10 proceeded with complete diastereoselectivity. The cyclohydrostannation of diesters 33 and 34 with hydrides 12 and 14 in all cases only afforded one stannylated macrocycle.
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: 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: 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
Taddols Like Unsaturated Diesters Stereoselective Cyclohydrostannation
Cyclohydrostannation
Eleven Membered Macrolides
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:11336/53818
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Synthesis of organotin derivatives of optically active eleven-membered macrodiolidesScoccia, JimenaGerbino, Darío CésarPodestá, Julio CesarTaddols Like Unsaturated Diesters Stereoselective CyclohydrostannationCyclohydrostannationEleven Membered Macrolideshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis and the results obtained in the hydrostannation of eight new TADDOL diacrylates and methacrylates are reported. The addition of triorganotin hydrides, R3SnH, 12-14 (R = nBu, neophyl, Ph, respectively) to diesters 6-11 containing different combinations of substituents at the C-2 carbon of the dioxolane ring, led to macrocyclization products in all cases. The cyclohydrostannation of diacrylate 10 proceeded with complete diastereoselectivity. The cyclohydrostannation of diesters 33 and 34 with hydrides 12 and 14 in all cases only afforded one stannylated macrocycle.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; ArgentinaFil: 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: 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; ArgentinaPergamon-Elsevier Science Ltd2016-05-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/53818Scoccia, Jimena; Gerbino, Darío César; Podestá, Julio Cesar; Synthesis of organotin derivatives of optically active eleven-membered macrodiolides; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 27; 7-8; 1-5-2016; 352-3600957-4166CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0957416616001051info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2016.02.014info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:44:26Zoai:ri.conicet.gov.ar:11336/53818instacron: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:34982025-09-03 09:44:27.109CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of organotin derivatives of optically active eleven-membered macrodiolides
title Synthesis of organotin derivatives of optically active eleven-membered macrodiolides
spellingShingle Synthesis of organotin derivatives of optically active eleven-membered macrodiolides
Scoccia, Jimena
Taddols Like Unsaturated Diesters Stereoselective Cyclohydrostannation
Cyclohydrostannation
Eleven Membered Macrolides
title_short Synthesis of organotin derivatives of optically active eleven-membered macrodiolides
title_full Synthesis of organotin derivatives of optically active eleven-membered macrodiolides
title_fullStr Synthesis of organotin derivatives of optically active eleven-membered macrodiolides
title_full_unstemmed Synthesis of organotin derivatives of optically active eleven-membered macrodiolides
title_sort Synthesis of organotin derivatives of optically active eleven-membered macrodiolides
dc.creator.none.fl_str_mv Scoccia, Jimena
Gerbino, Darío César
Podestá, Julio Cesar
author Scoccia, Jimena
author_facet Scoccia, Jimena
Gerbino, Darío César
Podestá, Julio Cesar
author_role author
author2 Gerbino, Darío César
Podestá, Julio Cesar
author2_role author
author
dc.subject.none.fl_str_mv Taddols Like Unsaturated Diesters Stereoselective Cyclohydrostannation
Cyclohydrostannation
Eleven Membered Macrolides
topic Taddols Like Unsaturated Diesters Stereoselective Cyclohydrostannation
Cyclohydrostannation
Eleven Membered Macrolides
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The synthesis and the results obtained in the hydrostannation of eight new TADDOL diacrylates and methacrylates are reported. The addition of triorganotin hydrides, R3SnH, 12-14 (R = nBu, neophyl, Ph, respectively) to diesters 6-11 containing different combinations of substituents at the C-2 carbon of the dioxolane ring, led to macrocyclization products in all cases. The cyclohydrostannation of diacrylate 10 proceeded with complete diastereoselectivity. The cyclohydrostannation of diesters 33 and 34 with hydrides 12 and 14 in all cases only afforded one stannylated macrocycle.
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: 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: 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 The synthesis and the results obtained in the hydrostannation of eight new TADDOL diacrylates and methacrylates are reported. The addition of triorganotin hydrides, R3SnH, 12-14 (R = nBu, neophyl, Ph, respectively) to diesters 6-11 containing different combinations of substituents at the C-2 carbon of the dioxolane ring, led to macrocyclization products in all cases. The cyclohydrostannation of diacrylate 10 proceeded with complete diastereoselectivity. The cyclohydrostannation of diesters 33 and 34 with hydrides 12 and 14 in all cases only afforded one stannylated macrocycle.
publishDate 2016
dc.date.none.fl_str_mv 2016-05-01
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/11336/53818
Scoccia, Jimena; Gerbino, Darío César; Podestá, Julio Cesar; Synthesis of organotin derivatives of optically active eleven-membered macrodiolides; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 27; 7-8; 1-5-2016; 352-360
0957-4166
CONICET Digital
CONICET
url http://hdl.handle.net/11336/53818
identifier_str_mv Scoccia, Jimena; Gerbino, Darío César; Podestá, Julio Cesar; Synthesis of organotin derivatives of optically active eleven-membered macrodiolides; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 27; 7-8; 1-5-2016; 352-360
0957-4166
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0957416616001051
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2016.02.014
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
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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
_version_ 1842268666899464192
score 13.13397

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