Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts

Detalhes bibliográficos
Autor(a) principal: Burke, Anthony
Data de Publicação: 2014
Outros Autores: Marques, Carolina, Schmalz, Hans-Günther, Mehmet, Dindaroglu
Tipo de documento: Artigo
Idioma: por
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10174/13447
https://doi.org/10.1039/c3ra47000h
Resumo: Herein we report the first application of Rh(I)-phosphane and phosphane-phosphite catalysts in the enantioselective catalytic arylation of ethyl glyoxylate with organoboron reagents, providing access to ethyl mandelate derivatives in high yield (up to 99%) and moderate to very good enantioselectivities (up to 75% ee). Commercial phosphane ligands, such as (R)-MonoPhos and (R)-Phanephos were tested, as well as non-commercial (R, R)-TADDOL-derived phosphane-phosphite ligands. Those ligands containing bulky substituents in the ortho-and para-positions of the chiral phosphite moiety were found to be the most selective.
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spelling Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalystsarilaçãoCatáliseHerein we report the first application of Rh(I)-phosphane and phosphane-phosphite catalysts in the enantioselective catalytic arylation of ethyl glyoxylate with organoboron reagents, providing access to ethyl mandelate derivatives in high yield (up to 99%) and moderate to very good enantioselectivities (up to 75% ee). Commercial phosphane ligands, such as (R)-MonoPhos and (R)-Phanephos were tested, as well as non-commercial (R, R)-TADDOL-derived phosphane-phosphite ligands. Those ligands containing bulky substituents in the ortho-and para-positions of the chiral phosphite moiety were found to be the most selective.2015-03-20T13:01:50Z2015-03-202014-02-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10174/13447http://hdl.handle.net/10174/13447https://doi.org/10.1039/c3ra47000hpor6035-60412046-20694RSC Advances12ajb@uevora.ptcarolsmarq@gmail.comschmalz@uni-koeln.demehmet.dindaroglu@uni-koeln.deAsymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts307Burke, AnthonyMarques, CarolinaSchmalz, Hans-GüntherMehmet, Dindarogluinfo: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:RCAAP2023-08-08T04:10:28ZPortal AgregadorONG
dc.title.none.fl_str_mv Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts
title Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts
spellingShingle Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts
Burke, Anthony
arilação
Catálise
title_short Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts
title_full Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts
title_fullStr Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts
title_full_unstemmed Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts
title_sort Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts
author Burke, Anthony
author_facet Burke, Anthony
Marques, Carolina
Schmalz, Hans-Günther
Mehmet, Dindaroglu
author_role author
author2 Marques, Carolina
Schmalz, Hans-Günther
Mehmet, Dindaroglu
author2_role author
author
author
dc.contributor.author.fl_str_mv Burke, Anthony
Marques, Carolina
Schmalz, Hans-Günther
Mehmet, Dindaroglu
dc.subject.por.fl_str_mv arilação
Catálise
topic arilação
Catálise
description Herein we report the first application of Rh(I)-phosphane and phosphane-phosphite catalysts in the enantioselective catalytic arylation of ethyl glyoxylate with organoboron reagents, providing access to ethyl mandelate derivatives in high yield (up to 99%) and moderate to very good enantioselectivities (up to 75% ee). Commercial phosphane ligands, such as (R)-MonoPhos and (R)-Phanephos were tested, as well as non-commercial (R, R)-TADDOL-derived phosphane-phosphite ligands. Those ligands containing bulky substituents in the ortho-and para-positions of the chiral phosphite moiety were found to be the most selective.
publishDate 2014
dc.date.none.fl_str_mv 2014-02-01T00:00:00Z
2015-03-20T13:01:50Z
2015-03-20
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/10174/13447
http://hdl.handle.net/10174/13447
https://doi.org/10.1039/c3ra47000h
url http://hdl.handle.net/10174/13447
https://doi.org/10.1039/c3ra47000h
dc.language.iso.fl_str_mv por
language por
dc.relation.none.fl_str_mv 6035-6041
2046-2069
4
RSC Advances
12
ajb@uevora.pt
carolsmarq@gmail.com
schmalz@uni-koeln.de
mehmet.dindaroglu@uni-koeln.de
Asymmetric catalytic arylation of ethyl glyoxylate using organoboron reagents and Rh(I)-phosphane and phosphane-phosphite catalysts
307
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
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instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
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reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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