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77951149397
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Several approaches to synthesize lactones via the phenonium ion intermediate were reported, however, application of phenonium ion in synthetic chemistry is rather unexplored. See
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Several approaches to synthesize lactones via the phenonium ion intermediate were reported, however, application of phenonium ion in synthetic chemistry is rather unexplored. See
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77951190706
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For methods to construct 4-substituted pyrrolo[1,2- a ]quinolines, see
-
For methods to construct 4-substituted pyrrolo[1,2- a ]quinolines, see
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19
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59649112358
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Murarka, S.; Zhang, C.; Konieczynska, M. D.; Seidel, D. Org. Lett. 2009, 11, 129-132 and references therein
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77951201136
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See the Supporting Information for details
-
See the Supporting Information for details.
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21
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77951169569
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For a comprehensive review dedicated to the N -acyliminium ion cyclization, see
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For a comprehensive review dedicated to the N -acyliminium ion cyclization, see
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22
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1842430777
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Maryanoff, B. E.; Zhang, H.-C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431-1628
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23
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77951171179
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19F NMR spectrum of the unpurified mixtures, 3aa (X = OTFA) was observed as the major product. The relative configuration was deduced from the hydrolyzed product (X = OH).
-
19F NMR spectrum of the unpurified mixtures, 3aa (X = OTFA) was observed as the major product. The relative configuration was deduced from the hydrolyzed product (X = OH).
-
-
-
-
24
-
-
77951167634
-
-
For the convenience of discussion, the nomenclature of cyclized products 3 and 4 is based on the core structures such as the quinoline ring and 1-benzazepine ring, respectively
-
For the convenience of discussion, the nomenclature of cyclized products 3 and 4 is based on the core structures such as the quinoline ring and 1-benzazepine ring, respectively.
-
-
-
-
25
-
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77951159555
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-
A free N -acyliminium ion intermediate should result in identical rate and product distribution; however, experimental results in Table 1 may imply a tight ion pair with the counterion or a complex with the Lewis acid used. This scenario was widely recognized in the Friedel-Crafts reaction
-
A free N -acyliminium ion intermediate should result in identical rate and product distribution; however, experimental results in Table 1 may imply a tight ion pair with the counterion or a complex with the Lewis acid used. This scenario was widely recognized in the Friedel-Crafts reaction; see
-
-
-
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28
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38149016915
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Oxonium ion
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Oxonium ion: Manner, J. A. M.; Cook, J. A., Jr.; Ramsey, B. G. J. Org. Chem. 1974, 39, 1199-1203
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77951152315
-
-
note
-
The neighboring effect of the methyl group is not clear. One proposed explanation is that the o -methyl group may participate in the stabilization of phenonium ion through a C-H hyperconjugation.
-
-
-
-
31
-
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77951159738
-
-
note
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However, the origin of exceedingly high stereoselectivity needs to be further investigated with the assistance of computational calculation.
-
-
-
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32
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77951179078
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note
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4.
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33
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0022026522
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For the β-effect of the silyl group, see
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For the β-effect of the silyl group, see: Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500
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Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
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Fleming, I.1
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77951195348
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note
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3 in 1,4-dioxane, however, this protocol resulted in inseparable alkene isomers; see
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36
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77951153435
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For selected complex natural products bearing pyrroloquinoline, see
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For selected complex natural products bearing pyrroloquinoline, see
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38
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70349978074
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Haplophytine
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Haplophytine: Ueda, H.; Satoh, H.; Matsumoto, K.; Sugimoto, K.; Fukuyama, T.; Tokuyama, H. Angew. Chem., Int. Ed. 2009, 48, 7600-7603
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41
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0020617257
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For an advance intermediate in the total synthesis of gephyrotoxin
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For an advance intermediate in the total synthesis of gephyrotoxin: Ito, Y.; Nakajo, E.; Nakatsuka, M.; Saegusa, T. Tetrahedron Lett. 1983, 24, 2881-2884
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