Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey

Autores
Simonetti, Sebastián Osvaldo; Pellegrinet, Silvina Carla
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The recent development of asymmetric organocatalytic C-C bond forming reactions involving organoboranes has attracted big interest in the synthetic community. Asymmetric organocatalytic additions to enones, aldehydes, ketones, imines, dienes, and related systems can be carried out with different organoboron compounds (boronic acids and esters and trifluoroborate salts) to give products with very good yields and enantiomeric ratios. In particular, many BINOL and α-hydroxyacid derivatives have been used as chiral organocatalysts. In this review, we describe the mechanisms that have been proposed based on theoretical and experimental studies for asymmetric organocatalytic C-C bond forming reactions with organoboron compounds. The mechanistic understanding that has been gained should contribute to the progress of this promising area of organic chemistry.
Fil: Simonetti, Sebastián Osvaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
ASYMMETRIC SYNTHESIS
DENSITY FUNCTIONAL CALCULATIONS
ORGANOBORON COMPOUNDS
ORGANOCATALYSIS
REACTION MECHANISMS
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:11336/106179
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic SurveySimonetti, Sebastián OsvaldoPellegrinet, Silvina CarlaASYMMETRIC SYNTHESISDENSITY FUNCTIONAL CALCULATIONSORGANOBORON COMPOUNDSORGANOCATALYSISREACTION MECHANISMShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The recent development of asymmetric organocatalytic C-C bond forming reactions involving organoboranes has attracted big interest in the synthetic community. Asymmetric organocatalytic additions to enones, aldehydes, ketones, imines, dienes, and related systems can be carried out with different organoboron compounds (boronic acids and esters and trifluoroborate salts) to give products with very good yields and enantiomeric ratios. In particular, many BINOL and α-hydroxyacid derivatives have been used as chiral organocatalysts. In this review, we describe the mechanisms that have been proposed based on theoretical and experimental studies for asymmetric organocatalytic C-C bond forming reactions with organoboron compounds. The mechanistic understanding that has been gained should contribute to the progress of this promising area of organic chemistry.Fil: Simonetti, Sebastián Osvaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaWiley VCH Verlag2019-05-26info: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/11336/106179Simonetti, Sebastián Osvaldo; Pellegrinet, Silvina Carla; Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey; Wiley VCH Verlag; European Journal of Organic Chemistry; 2019; 19; 26-5-2019; 2956-29701434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201900029info:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201900029info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:04:45Zoai:ri.conicet.gov.ar:11336/106179instacron: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:34982025-10-15 15:04:45.43CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey
title Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey
spellingShingle Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey
Simonetti, Sebastián Osvaldo
ASYMMETRIC SYNTHESIS
DENSITY FUNCTIONAL CALCULATIONS
ORGANOBORON COMPOUNDS
ORGANOCATALYSIS
REACTION MECHANISMS
title_short Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey
title_full Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey
title_fullStr Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey
title_full_unstemmed Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey
title_sort Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey
dc.creator.none.fl_str_mv Simonetti, Sebastián Osvaldo
Pellegrinet, Silvina Carla
author Simonetti, Sebastián Osvaldo
author_facet Simonetti, Sebastián Osvaldo
Pellegrinet, Silvina Carla
author_role author
author2 Pellegrinet, Silvina Carla
author2_role author
dc.subject.none.fl_str_mv ASYMMETRIC SYNTHESIS
DENSITY FUNCTIONAL CALCULATIONS
ORGANOBORON COMPOUNDS
ORGANOCATALYSIS
REACTION MECHANISMS
topic ASYMMETRIC SYNTHESIS
DENSITY FUNCTIONAL CALCULATIONS
ORGANOBORON COMPOUNDS
ORGANOCATALYSIS
REACTION MECHANISMS
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 recent development of asymmetric organocatalytic C-C bond forming reactions involving organoboranes has attracted big interest in the synthetic community. Asymmetric organocatalytic additions to enones, aldehydes, ketones, imines, dienes, and related systems can be carried out with different organoboron compounds (boronic acids and esters and trifluoroborate salts) to give products with very good yields and enantiomeric ratios. In particular, many BINOL and α-hydroxyacid derivatives have been used as chiral organocatalysts. In this review, we describe the mechanisms that have been proposed based on theoretical and experimental studies for asymmetric organocatalytic C-C bond forming reactions with organoboron compounds. The mechanistic understanding that has been gained should contribute to the progress of this promising area of organic chemistry.
Fil: Simonetti, Sebastián Osvaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Pellegrinet, Silvina Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description The recent development of asymmetric organocatalytic C-C bond forming reactions involving organoboranes has attracted big interest in the synthetic community. Asymmetric organocatalytic additions to enones, aldehydes, ketones, imines, dienes, and related systems can be carried out with different organoboron compounds (boronic acids and esters and trifluoroborate salts) to give products with very good yields and enantiomeric ratios. In particular, many BINOL and α-hydroxyacid derivatives have been used as chiral organocatalysts. In this review, we describe the mechanisms that have been proposed based on theoretical and experimental studies for asymmetric organocatalytic C-C bond forming reactions with organoboron compounds. The mechanistic understanding that has been gained should contribute to the progress of this promising area of organic chemistry.
publishDate 2019
dc.date.none.fl_str_mv 2019-05-26
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/11336/106179
Simonetti, Sebastián Osvaldo; Pellegrinet, Silvina Carla; Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey; Wiley VCH Verlag; European Journal of Organic Chemistry; 2019; 19; 26-5-2019; 2956-2970
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/106179
identifier_str_mv Simonetti, Sebastián Osvaldo; Pellegrinet, Silvina Carla; Asymmetric Organocatalytic C-C Bond Forming Reactions with Organoboron Compounds: A Mechanistic Survey; Wiley VCH Verlag; European Journal of Organic Chemistry; 2019; 19; 26-5-2019; 2956-2970
1434-193X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201900029
info:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201900029
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
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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 13.22299

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