Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10174/31399 https://doi.org/10.1002/ejoc.202000334 |
Resumo: | A one-step, three-component Petasis reaction of isatin derived 5-arylboronate-3-substituted oxindole derivatives with salicylaldehydes and secondary amines affords new enan- tiomerically pure structurally diverse 5-α-(3-substituted-oxind- ole)-benzylamine derivatives. The reaction shows good sub- strate and reagent scope affording the products with good to excellent yields (up to >99 % yield) and enantioselectivities (upto 99 % ee) using cheap and readily available (R)-BINOL as the organocatalyst. A diastereoselective version of the reaction was also developed where moderate yields (37 to 55 % yield), excel- lent enantioselectivities (up to 99 % ee) and good diastereo- selectivities (up to 86 % de) were obtained for new 5-α-(3- hydroxy-oxindole)-benzylamine derivatives, having two stereo- centers. The reaction is also feasible on gram-scale. |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis ReactionPetasisIsatinBINOLoxindoleStereoselectivityA one-step, three-component Petasis reaction of isatin derived 5-arylboronate-3-substituted oxindole derivatives with salicylaldehydes and secondary amines affords new enan- tiomerically pure structurally diverse 5-α-(3-substituted-oxind- ole)-benzylamine derivatives. The reaction shows good sub- strate and reagent scope affording the products with good to excellent yields (up to >99 % yield) and enantioselectivities (upto 99 % ee) using cheap and readily available (R)-BINOL as the organocatalyst. A diastereoselective version of the reaction was also developed where moderate yields (37 to 55 % yield), excel- lent enantioselectivities (up to 99 % ee) and good diastereo- selectivities (up to 86 % de) were obtained for new 5-α-(3- hydroxy-oxindole)-benzylamine derivatives, having two stereo- centers. The reaction is also feasible on gram-scale.WILEY-VCH Verlag GmbH & Co. KGaA2022-03-22T11:47:38Z2022-03-222020-05-25T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10174/31399http://hdl.handle.net/10174/31399https://doi.org/10.1002/ejoc.202000334enghttps://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202000334carolsmarq@uevora.ptndndajb@uevora.pt307Marques, Carolina SilvaMcArdle, PatrickErxleben, AndreaBurke, Anthony J.info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-08-08T04:45:07ZPortal AgregadorONG |
dc.title.none.fl_str_mv |
Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction |
title |
Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction |
spellingShingle |
Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction Marques, Carolina Silva Petasis Isatin BINOL oxindole Stereoselectivity |
title_short |
Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction |
title_full |
Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction |
title_fullStr |
Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction |
title_full_unstemmed |
Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction |
title_sort |
Accessing New 5-α-(3,3-Disubstituted Oxindole)-Benzylamine Derivatives from Isatin: Stereoselective Organocatalytic Three Component Petasis Reaction |
author |
Marques, Carolina Silva |
author_facet |
Marques, Carolina Silva McArdle, Patrick Erxleben, Andrea Burke, Anthony J. |
author_role |
author |
author2 |
McArdle, Patrick Erxleben, Andrea Burke, Anthony J. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Marques, Carolina Silva McArdle, Patrick Erxleben, Andrea Burke, Anthony J. |
dc.subject.por.fl_str_mv |
Petasis Isatin BINOL oxindole Stereoselectivity |
topic |
Petasis Isatin BINOL oxindole Stereoselectivity |
description |
A one-step, three-component Petasis reaction of isatin derived 5-arylboronate-3-substituted oxindole derivatives with salicylaldehydes and secondary amines affords new enan- tiomerically pure structurally diverse 5-α-(3-substituted-oxind- ole)-benzylamine derivatives. The reaction shows good sub- strate and reagent scope affording the products with good to excellent yields (up to >99 % yield) and enantioselectivities (upto 99 % ee) using cheap and readily available (R)-BINOL as the organocatalyst. A diastereoselective version of the reaction was also developed where moderate yields (37 to 55 % yield), excel- lent enantioselectivities (up to 99 % ee) and good diastereo- selectivities (up to 86 % de) were obtained for new 5-α-(3- hydroxy-oxindole)-benzylamine derivatives, having two stereo- centers. The reaction is also feasible on gram-scale. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-05-25T00:00:00Z 2022-03-22T11:47:38Z 2022-03-22 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10174/31399 http://hdl.handle.net/10174/31399 https://doi.org/10.1002/ejoc.202000334 |
url |
http://hdl.handle.net/10174/31399 https://doi.org/10.1002/ejoc.202000334 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202000334 carolsmarq@uevora.pt nd nd ajb@uevora.pt 307 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
WILEY-VCH Verlag GmbH & Co. KGaA |
publisher.none.fl_str_mv |
WILEY-VCH Verlag GmbH & Co. KGaA |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
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repository.mail.fl_str_mv |
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_version_ |
1777304659963150336 |