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Titolo:
Selective synthesis of cis-2-vinyl-3-alkylaziridines and 3-pyrrolines fromcommon intermediates (Z)-4-N arylsulfonylaminoalk-2-en-1-ols
Autore:
Ishii, K; Ohno, H; Takemoto, Y; Osawa, E; Yamaoka, Y; Fujii, N; Ibuka, T;
Indirizzi:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ Kyoto Japan 6068501 aceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kobe Gakuin Univ, Fac Pharmaceut Sci, Nishi Ku, Kobe, Hyogo 6512180, JapanKobe Gakuin Univ Kobe Hyogo Japan 6512180 Ku, Kobe, Hyogo 6512180, Japan
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 15, , anno: 1999,
pagine: 2155 - 2163
SICI:
0300-922X(19990807):15<2155:SSOCA3>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
(E)-ALKENE DIPEPTIDE ISOSTERES; PALLADIUM(0)-CATALYZED EQUILIBRATION REACTIONS; ENANTIOSELECTIVE TOTAL SYNTHESIS; AZA-<2,3>-WITTIG REARRANGEMENTS; ORGANOCOPPER REAGENTS; THERMODYNAMIC PREFERENCE; PYRROLINE ANNULATION; ASYMMETRIC-SYNTHESIS; AZIRIDINES BEARING; VINYLAZIRIDINES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
43
Recensione:
Indirizzi per estratti:
Indirizzo: Ishii, K Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ Kyoto Japan 6068501 , Sakyo Ku, Kyoto 6068501, Japan
Citazione:
K. Ishii et al., "Selective synthesis of cis-2-vinyl-3-alkylaziridines and 3-pyrrolines fromcommon intermediates (Z)-4-N arylsulfonylaminoalk-2-en-1-ols", J CHEM S P1, (15), 1999, pp. 2155-2163

Abstract

A simple method for the synthesis of both cis-2-vinylaziridines and 3-pyrrolines from common intermediate (Z)-4-(N-arylsulfonyl)amino-4-alkylbut-2-en-1-ols, is described. Palladium(0)-catalyzed reactions of methyl carbonatesof the N-protected (Z)-4-amino-4-alkylbut-2-en-1-ols yield predominantly cis-3-alkyl-2-vinylaziridines. Alternatively, upon exposure to sodium hydride, methanesulfonates derived from N-protected (Z)-4-amino-4-alkylbut-2-en-1-ols give exclusively the corresponding 3-pyrrolines in high yields. A synthesis of biologically important (S)-3,4-dehydroproline is also presented.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/09/20 alle ore 08:21:53