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Titolo:
Stereoselective synthesis of 2-alkenylaziridines and 2-alkenylazetidines by palladium-catalyzed intramolecular amination of alpha- and beta-amino allenes
Autore:
Ohno, H; Anzai, M; Toda, A; Ohishi, S; Fujii, N; Tanaka, T; Takemoto, Y; Ibuka, T;
Indirizzi:
Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan Osaka Univ Suita Osaka Japan 5650871 eut Sci, Suita, Osaka 5650871, Japan Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ Kyoto Japan 6068501 aceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 14, volume: 66, anno: 2001,
pagine: 4904 - 4914
SICI:
0022-3263(20010713)66:14<4904:SSO2A2>2.0.ZU;2-Q
Fonte:
ISI
Lingua:
ENG
Soggetto:
HYPERVALENT IODONIUM SALTS; (E)-ALKENE DIPEPTIDE ISOSTERES; ASYMMETRIC-SYNTHESIS; CYCLIZATION REACTION; EFFICIENT SYNTHESIS; CYCLOPROPANATION REACTIONS; ENANTIOSELECTIVE SYNTHESIS; THERMODYNAMIC PREFERENCE; ORGANOCOPPER REAGENTS; COUPLING-CYCLIZATION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
83
Recensione:
Indirizzi per estratti:
Indirizzo: Tanaka, T Osaka Univ, Grad Sch Pharmaceut Sci, 1-6 Yamadaoka, Suita, Osaka5650871, Japan Osaka Univ 1-6 Yamadaoka Suita Osaka Japan 5650871 650871, Japan
Citazione:
H. Ohno et al., "Stereoselective synthesis of 2-alkenylaziridines and 2-alkenylazetidines by palladium-catalyzed intramolecular amination of alpha- and beta-amino allenes", J ORG CHEM, 66(14), 2001, pp. 4904-4914

Abstract

Whereas palladium-catalyzed reaction of N-arylsulfonyl-alpha -amino allenes with an aryl iodide (4 equiv) in the presence of potassium carbonate (4 equiv) in DMF at around 70 degreesC affords the corresponding 3-pyrroline derivatives, the reaction in refluxing 1,4-dioxane under otherwise identical conditions yields exclusively or most predominantly the corresponding 2-alkenylaziridines bearing an aryl group on the double bond. Similarly, N-arylsulfonyl-beta -amino allenes can be also cyclized into the corresponding alkenylazetidines bearing a 2,4-cis-configuration under palladium-catalyzed cyclization conditions in DMF.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 26/09/20 alle ore 05:34:17