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J-GLOBAL ID：200902215532213680   Reference number：07A1062325

INVESTIGATION OF THE REGIOSELECTIVITY ON THE REACTION OF 2-INDOLYLCYANOCUPRATE WITH N-(PROP-2-EN-1-YLIDENE)AMINIUM CHLORIDE DERIVATIVES

2-インドリルシアノクプラートとN-(プロパ-2-エン-1-イリデン)アミニウムクロリド誘導体の反応における位置選択性の検討

Author (5)： ISHIKURA Minoru (Health Sci. Univ. Hokkaido, Hokkaido, JPN) ,  KOMATSU Hiroyuki (Health Sci. Univ. Hokkaido, Hokkaido, JPN) ,  YAMADA Koji (Health Sci. Univ. Hokkaido, Hokkaido, JPN) ,  ABE Takumi (Health Sci. Univ. Hokkaido, Hokkaido, JPN) ,  YANADA Reiko (Hiroshima Internatiional Univ., Hiroshima, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 71  Issue： 11  Page： 2325-2329  Publication year： Nov. 01, 2007 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *copper complex ,...
Semi thesaurus term： metathesis

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JST classification (4)： Complexes of 9 and 10 groups  (CE01050Y) ,  Group 11 and group 12 organic compounds  (CF09052N) ,  Aromatic monocyclic aldehydes  (CF05160X) ,  Regiochemistry of organic reaction  (CF02140G)

Substance index (18)： [1-(1-Methyl-1H-indole-3-yl)-2-methyl-3-phenylallyl]isobutylcarbamic acid phenyl ester ,  [1-(1-Methyl-1H-indole-3-yl)-3,3-diphenylallyl]benzylcarbamic acid phenyl ester ,  [1-(1-Methyl-1H-indole-3-yl)-3-phenylallyl]isobutylcarbamic acid phenyl ester ,  [1-(1-Methyl-1H-indole-3-yl)-3-phenyl-2-butenyl]benzylcarbamic acid phenyl ester ,  [1-(1-Methyl-1H-indole-3-yl)-3-methyl-2-butenyl]benzylcarbamic acid phenyl ester ,  Benzyl[1-(1-methyl-2-allyl-1H-indole-3-yl)-3-methyl-2-butenyl]carbamic acid phenyl ester ,  [3-(1-Methyl-1H-indole-3-yl)-3-phenyl-1-propenyl]isobutylcarbamic acid phenyl ester ,  1-Methyl-1H-indole ,  Hempa ,  N-(2-Methyl-3-phenylallylidene)-N-(phenoxycarbonyl)-2-methylpropane-1-aminium ,  N-(3,3-Diphenylallylidene)-N-(phenoxycarbonyl)benzenemethaneaminium ,  N-(3-Phenylallylidene)-N-(phenoxycarbonyl)-2-methylpropane-1-aminium ,  N-(3-Phenyl-2-butene-1-ylidene)-N-(phenoxycarbonyl)benzenemethaneaminium ,  N-Benzyl-3-methyl-2-butene-1-imine ,  tert-Butyllithium ,  Allyl bromide ,  Chloroformic acid phenyl ,  Benzyl(1,4-dihydro-9-methyl-9H-carbazole-4-yl)carbamic acid phenyl ester

Reference (8)：

• B. H. Lipshutz and S. Sengupta,‘Organic Reactions: Organocopper Reagents: Substitution, Conjugate Addition, Carbo/Metallocupration, and Other Reactions,’ Vol.41, ed. by L. A. Paquette, John Wiley&Sons, Inc., New York, 1992, pp. 135-631; A. Sundararaman and F. Jakle, J. Organomet. Chem., 2003, 681, 134; V. Caprio, Lett. in Org. Chem., 2006, 3, 339; X. Yang and P. Knochel, Synthesis, 2006, 2618; G. Dunet and P. Knochel, Synlett, 2006, 407; T. J. Korn, M. A. Schade, S. Wirth, and P. Knochel, Org. Lett., 2006, 8, 725; M. Kienle, D. S. Reddy, V. Amo, and P. Knochel, Synthesis, 2007, 1272.
• K. Sestanj, E. Melenski, and I. Jirkovsky, Tetrahedron Lett., 1994, 35, 5417; B. F. Bonini, M. Fochi, M. C. Franchini, G. Mazzanti, A. Ricci, J. P. Picard, J. Dunogues, J. M. Aizpurua, and C. Palomo, Synlett, 1997, 1321; R. Reinhard, M. Glaser, R. Neumann, and G. Maas, J. Org. Chem., 1997, 62, 7744; M. Kitamura, S. Chiba, and K. Narasaka, Chem. Lett., 2004, 33, 942; D. L. J. Clive and D. Liu, Tetrahedron Lett., 2005, 46, 5305; A. K. Miller, C. C. Hughes, J. J. Kennedy-Smith, S. N. Gradl, and D. Trauner, J. Am. Chem. Soc., 2006, 128, 17057.
• M. Ishikura, R. Uemura, K. Yamada, and R. Yanada, Heterocycles, 2006, 68, 2349.
• NOE Correlations of 6c-e and 8:
• 5e: ¹H-NMR (CDCl₃) δ: 1.71 (s, 3H), 1.77 (s, 3H), 3.76 (s, 3H), 4.31 (m, 1H), 4.61 (d, 1H, J=16.1 Hz), 5.56 (d, 1H, J=8.6 Hz), 6.58 (br s, 1H), 6.90-7.41 (m, 14H), 7.73 (br s, 1H). ¹³C-NMR (CDCl₃) δ: 18.6, 25.8, 32.9, 47.4, 51.6, 109.4, 114.1, 119.6, 119.9, 121.9, 122.1, 125.2, 126.6, 127.1, 128.1, 129.3, 136.3, 137.5, 139.7, 151.6, 155.1. 6e: ¹H-NMR (CDCl₃) δ: 1.51 (s, 6H), 3.65 (s, 3H), 4.93 (d, 2H, J=17.9 Hz), 5.41 (d, 1H, J=14.9 Hz), 6.42 and 6.52 (two s, 1H), 7.00-7.43 (m, 14H), 7.61 (d, 1H, J=8.1 Hz). ¹³C-NMR (CDCl₃) δ: 29.2, 32.6, 35.8, 48.4, 109.4, 118.5, 121.2, 121.3, 121.8, 123.0, 123.2, 124.2, 125.0, 125.1, 125.7, 126.6, 127.2, 127.3, 128.7, 129.4, 137.2, 137.8, 151.2, 151.4, 153.3.

Terms in the title (2)： 誘導体 ,  位置選択性