Crucial role of beta-elimination in determining regio- and chemoselectivity of the rhodium-catalyzed hydroformylation of N-allylpyrroles: a new approach to 5,6-dihydroindolizines (Articolo in rivista)

Type

• Prodotto della ricerca (Classe)
• Articolo in rivista (Classe)

Label

• Crucial role of beta-elimination in determining regio- and chemoselectivity of the rhodium-catalyzed hydroformylation of N-allylpyrroles: a new approach to 5,6-dihydroindolizines (Articolo in rivista) (literal)

Anno

• 2010-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1055/s-0030-1257860 (literal)

Alternative label

• Settambolo R. (2010)
  Crucial role of beta-elimination in determining regio- and chemoselectivity of the rhodium-catalyzed hydroformylation of N-allylpyrroles: a new approach to 5,6-dihydroindolizines
  in Synthesis (Stuttg.)
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Settambolo R. (literal)

Pagina inizio

• 2915 (literal)

Pagina fine

• 2921 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#altreInformazioni

• Prodotto digitalizzato (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 17 (literal)

Rivista

• Synthesis (Rivista)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• ICCOM-CNR UOS di Pisa (literal)

Titolo

• Crucial role of beta-elimination in determining regio- and chemoselectivity of the rhodium-catalyzed hydroformylation of N-allylpyrroles: a new approach to 5,6-dihydroindolizines (literal)

Abstract

• Rhodium-catalyzed hydroformylation of the chiral (S)-3-alkyl-3-pyrrol-1- ylprop-1-enes at 100 atmospheres total pressure and 25C led to the preferential formation of the branched 3-alkyl-2-methyl-3-pyrrol-1-ylpropanals. At 30 atmospheres and 125°C, the linear 4-alkyl-4-pyrrol-1-ylbutanals were obtained: these aldehydes are not the final products, but evolve into more stable 5,6-dihydroindolizines, with the same optical purity as the starting olefins, via a domino cyclization-dehydration process. According to the generally accepted mechanism for rhodium-catalyzed hydroformylation, the regioselectivity, and then the final chemoselectivity, can be rationalized by taking into account that while at room temperature no -elimination occurs, at high temperature the -elimination involves the branched rhodium-alkyl intermediate only. © 2010 Georg Thieme Verlag Stuttgart New York. (literal)

Prodotto di

• Istituto di chimica dei composti organo metallici (ICCOM) (Istituto)
• Sostenibilità in processi selettivi: catalizzatori, metodologie e approcci innovativi (PM.P03.002.001) (Modulo)

Autore CNR

• ROBERTA SETTAMBOLO (Unità di personale interno)

Insieme di parole chiave

• Parole chiave di "Crucial role of beta-elimination in determining regio- and chemoselectivity of the rhodium-catalyzed hydroformylation of N-allylpyrroles: a new approach to 5,6-dihydroindolizines" (Insieme di parole chiave)

Incoming links:

Prodotto

• Istituto di chimica dei composti organo metallici (ICCOM) (Istituto)
• Sostenibilità in processi selettivi: catalizzatori, metodologie e approcci innovativi (PM.P03.002.001) (Modulo)

Autore CNR di

• ROBERTA SETTAMBOLO (Unità di personale interno)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Synthesis (Rivista)

Insieme di parole chiave di

• Parole chiave di "Crucial role of beta-elimination in determining regio- and chemoselectivity of the rhodium-catalyzed hydroformylation of N-allylpyrroles: a new approach to 5,6-dihydroindolizines" (Insieme di parole chiave)