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Titolo:
Remote dipole effects as a means to accelerate [Ru(amino alcohol)]-catalyzed transfer hydrogenation of ketones
Autore:
Nordin, SJM; Roth, P; Tarnai, T; Alonso, DA; Brandt, P; Andersson, PG;
Indirizzi:
Uppsala Univ, Dept Organ Chem, S-75121 Uppsala, Sweden Uppsala Univ Uppsala Sweden S-75121 Organ Chem, S-75121 Uppsala, Sweden Univ Alicante, Dept Quim Organ, E-03080 Alicante, Spain Univ Alicante Alicante Spain E-03080 Quim Organ, E-03080 Alicante, Spain Karo Bio AB, Dept Med & Computat Chem, S-14157 Huddinge, Sweden Karo Bio AB Huddinge Sweden S-14157 putat Chem, S-14157 Huddinge, Sweden
Titolo Testata:
CHEMISTRY-A EUROPEAN JOURNAL
fascicolo: 7, volume: 7, anno: 2001,
pagine: 1431 - 1436
SICI:
0947-6539(20010401)7:7<1431:RDEAAM>2.0.ZU;2-#
Fonte:
ISI
Lingua:
ENG
Soggetto:
ASYMMETRIC TRANSFER HYDROGENATION; AROMATIC KETONES; EFFICIENT; ALCOHOLS; CATALYSIS; LIGANDS; COMPLEXES;
Keywords:
amino alcohols; asymmetric catalysis; reduction; ruthenium;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
24
Recensione:
Indirizzi per estratti:
Indirizzo: Andersson, PG Uppsala Univ, Dept Organ Chem, Box 531, S-75121 Uppsala, Sweden Uppsala Univ Box 531 Uppsala Sweden S-75121 Uppsala, Sweden
Citazione:
S.J.M. Nordin et al., "Remote dipole effects as a means to accelerate [Ru(amino alcohol)]-catalyzed transfer hydrogenation of ketones", CHEM-EUR J, 7(7), 2001, pp. 1431-1436

Abstract

A new generation of 2-azanolbornyl amino alcohol ligands for the catalytictransfer hydrogenation reaction of aromatic ketones was synthesized. Extremely active catalysts were formed by introducing a ketal functionality at the I car end of the ligand, Acetophenone was reduced in 96% cc at low catalyst loading, substrate: to catalyst ratio, S/C 5000, within 90 minutes withisopropyl alcohol as the hydrogen donor. It was round that the dioxolane substituent in the ligand increased the turnover frequency, TOF50 from 1050 h(-1) to 3000 h(-1) at an S/C ratio of 1000, Introduction of a methyl groupat the carbinol carbon resulted in TOF50 as high as 8500 h(-1), Transfer hydrogenation of a range of aromatic ketones was evaluated and found to reach completion within 30 minutes at room temperature, and excellent enantioselectivity, up to 99% cc, was obtained. A possible explanation for the enhanced activity was provided by density functional calculations, which showed that the presence of a remote dipole in the ligand lowered the transition state energy.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 01/04/20 alle ore 11:30:01