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J-GLOBAL ID：200902149784059680   Reference number：02A0669359

Synthesis of Dihydropyrrole Derivatives by Copper-Catalyzed Cyclization of γ, δ-Unsaturated Ketone O-Methoxycarbonyloximes.

γ,δ-不飽和ケトンO-メトキシカルボニルオキシムの銅接触環化によるジヒドロピロール誘導体の合成

Author (3)： KOGANEMARU Y (Univ. Tokyo, Tokyo) ,  KITAMURA M (Univ. Tokyo, Tokyo) ,  NARASAKA K (Univ. Tokyo, Tokyo)
Material： Chemistry Letters  (Chem Lett)
Issue： 8  Page： 784-785  Publication year： Aug. 05, 2002 
JST Material Number： S0742A  ISSN： 0366-7022  CODEN： CMLTAG  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： chemical synthesis ,...

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JST classification (1)： Pyrroles  (CF07076L)

Substance index (25)： Dimethyl sulfide ,  1-Phenyl-6-heptene-3-one (E)-O-(methoxycarbonyl)oxime ,  1-Phenyl-6-heptene-3-one (Z)-O-(methoxycarbonyl)oxime ,  2-Phenethyl-5-methyl-1-pyrroline ,  2-Phenethyl-5-(phenylthiomethyl)-1-pyrroline ,  2-Phenethyl-5-(bromomethyl)-1-pyrroline ,  2-Phenethyl-5-(chloromethyl)-1-pyrroline ,  Tris(trimethylsilyl)silane ,  Diphenyl persulfide ,  1-Phenyl-6-heptene-3-one (E)-O-(pentafluorobenzoyl)oxime ,  1-Phenyl-6-heptene-3-one (Z)-O-(pentafluorobenzoyl)oxime ,  (6E)-1-Phenyl-6-octene-3-one (E)-O-(methoxycarbonyl)oxime ,  (6E)-1-Phenyl-6-octene-3-one (Z)-O-(methoxycarbonyl)oxime ,  (6E)-1,7-Diphenyl-6-heptene-3-one (E)-O-(methoxycarbonyl)oxime ,  (6E)-1,7-Diphenyl-6-heptene-3-one (Z)-O-(methoxycarbonyl)oxime ,  1-Phenyl-6-methyl-6-heptene-3-one (E)-O-(methoxycarbonyl)oxime ,  1-Phenyl-6-methyl-6-heptene-3-one (Z)-O-(methoxycarbonyl)oxime ,  1-Phenyl-4-pentene-1-one O-(methoxycarbonyl)oxime ,  2-(Methoxycarbonyloxyimino)-5-hexenoic acid ethyl ester ,  2-Phenethyl-5-(1-bromoethyl)-1-pyrroline ,  2-Phenethyl-5-(α-bromobenzyl)-1-pyrroline ,  2-Phenethyl-5-methyl-5-(bromomethyl)-1-pyrroline ,  2-Phenethyl-5-methylpyridine ,  2-Phenyl-5-(bromomethyl)-1-pyrroline ,  5-(Bromomethyl)-1-pyrroline-2-carboxylic acid ethyl ester

Reference (17)：

• 1) K. Uchiyama, Y. Hayashi, and K. Narasaka, Chem. Lett., 1998, 1261.
• 2) J. Boivin, A.-M. Schiano, S. Z. Zard, and H. Zhang, Tetrahedron Lett., 40, 4531 (1999).
• 3) In recent years, there have been some reports on the radical addition of trichloromethyl carbonyl compounds to intramolecular olefin moiety mediated by a catalytic amount of copper complexes of bipyridine,^3a,b N-alkyl-2-pyridylmetanimine,^3c,d or multidentate amines^3c,e,f as redox catalysts. a) H. Nagashima, Y. Isono, and S. Iwamatsu, J. Org. Chem., 66, 315 (2001).
•  b) S. Iwamatsu, H. Kondo, K. Matsubara, and H. Nagashima, Tetrahedron, 55, 1687 (1999).
•  c) A. J. Clark, R. P. Filik, and G. H. Thomas, Tetrahedron Lett., 40, 4885 (1999).

Terms in the title (4)： 不飽和ケトン ,  銅 ,  環化 ,  誘導体