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Titolo:
Oxidative homocoupling of chiral 3-arylpropanoic acid derivatives. Application to asymmetric synthesis of lignans
Autore:
Kise, N; Ueda, T; Kumada, K; Terao, Y; Ueda, N;
Indirizzi:
Tottori Univ, Fac Engn, Dept Biotechnol, Tottori 6800945, Japan Tottori Univ Tottori Japan 6800945 pt Biotechnol, Tottori 6800945, Japan
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 2, volume: 65, anno: 2000,
pagine: 464 - 468
SICI:
0022-3263(20000128)65:2<464:OHOC3A>2.0.ZU;2-Y
Fonte:
ISI
Lingua:
ENG
Soggetto:
ENANTIOSELECTIVE TOTAL SYNTHESIS; TANDEM CONJUGATE ADDITION; STEREOSELECTIVE SYNTHESIS; (-)-HINOKININ; LACTONES; (-)-ENTEROLACTONE; ALKYLATION; IODINE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
34
Recensione:
Indirizzi per estratti:
Indirizzo: Kise, N Tottori Univ, Fac Engn, Dept Biotechnol, Tottori 6800945, Japan Tottori Univ Tottori Japan 6800945 chnol, Tottori 6800945, Japan
Citazione:
N. Kise et al., "Oxidative homocoupling of chiral 3-arylpropanoic acid derivatives. Application to asymmetric synthesis of lignans", J ORG CHEM, 65(2), 2000, pp. 464-468

Abstract

The oxidative homocouplings of lithium enolates of (4S)-3-(3-arylpropanoyl)-4-isopropyl-2-oxazolidinones and (4R,5S)-1-(3-arylpropanoyl)-3,4-dimethyl-5-phenyl-2-imidazolidinones gave the corresponding R,R-dimers stereoselectively with TiCl4, PhI(OAc)(2), or CuCl2 as an oxidant. The stereoselectivity can be explained by a radical coupling mechanism. Optically active dibenzylbutyrolactone lignans, such as (-)-hinokinin and (-)-dimethylmatairesinol, and dibenzylbutanediol lignans, such as (-)-dihydrocubebin and (-)-dimethylsecoisolariciresinol, were synthesized from the major R,R-dimers. The oxidative coupling of (4R,5S)-1-(3-arylpropanoyl)-3,4-dimethyl 2-imidazolidinones with LDA-I-2 gave R,S-dimers mainly, and this result can be explained by an S(N)2 mechanism.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/01/20 alle ore 18:43:49