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Titolo:
Highly efficient enantioselective epoxidation of alpha,beta-enones catalyzed by cheap chiral lanthanum and gadolinium alkoxides
Autore:
Chen, RF; Qian, CT; de Vries, JG;
Indirizzi:
DSM Res & Patents, Dept LS 2CC, NL-6160 MD Geleen, Netherlands DSM Res & Patents Geleen Netherlands NL-6160 MD 0 MD Geleen, Netherlands Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China Chinese Acad Sci Shanghai Peoples R China 200032 200032, Peoples R China
Titolo Testata:
TETRAHEDRON
fascicolo: 49, volume: 57, anno: 2001,
pagine: 9837 - 9842
SICI:
0040-4020(200112)57:49<9837:HEEEOA>2.0.ZU;2-F
Fonte:
ISI
Lingua:
ENG
Soggetto:
ASYMMETRIC EPOXIDATION; ALPHA,BETA-UNSATURATED KETONES; ALDEHYDES; ENONES; COMPLEX; OLEFINS; CHALCONE; ACIDS; CHAIN; BINOL;
Keywords:
asymmetric epoxidation; alpha,beta-enones; chiral lanthanoid complexes;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
37
Recensione:
Indirizzi per estratti:
Indirizzo: de Vries, JG DSM Res & Patents, Dept LS 2CC, POB 18, NL-6160 MD Geleen, Netherlands DSM Res & Patents POB 18 Geleen Netherlands NL-6160 MD lands
Citazione:
R.F. Chen et al., "Highly efficient enantioselective epoxidation of alpha,beta-enones catalyzed by cheap chiral lanthanum and gadolinium alkoxides", TETRAHEDRON, 57(49), 2001, pp. 9837-9842

Abstract

(S)-6,6'-Dibromo-BINOL and (S)-6,6'-diphenyl-BINOL have been developed as efficient chiral ligands applicable to lanthanoid catalyzed asymmetric epoxidation of alpha,beta -unsaturated ketones in the presence of cumene hydroperoxide. Excellent chemical yield and enantioselectivity have been achievedfor several epoxides at room temperature by using 5 mol% of La(O-i-Pr)(3)-(S)-6,6'-dibromo-BINOL and Gd(O-i-Pr)3-(S)-6,6'-diphenyl-BINOL, respectively. Up to 95% ee was obtained for epoxychalcone with Gd(O-i-Pr)(3)-(S)-6,6-diphenyl-BINOL catalyst at room temperature. A plausible catalyst structure as well as the catalytic cycle has also been suggested. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 26/11/20 alle ore 14:30:23