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In agreement with literature data, only decomposition products were obtained in the reactions of N-tosyl, N-(2-thienylsulfonyl, and N-(2-pyridylsulfonyl)imines of benzaldehyde with 5 in the presence of 10 mol% of Cu(OTf)2 after 48 hours at room temperature
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2 after 48 hours at room temperature.
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63849268502
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Amounts of dienophile lower than 20 equivalents led to incomplete conversions
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Amounts of dienophile lower than 20 equivalents led to incomplete conversions.
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52
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63849205255
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Similar enantioselectivities were obtained in other solvents, such as toluene (61% ee, 1,2-dichloroethane (62% ee, tetrahydrofuran (58% ee, or 1,4-dioxane 60% ee
-
Similar enantioselectivities were obtained in other solvents, such as toluene (61% ee), 1,2-dichloroethane (62% ee), tetrahydrofuran (58% ee), or 1,4-dioxane (60% ee).
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, or THF).
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0037073238
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2O and DBFOX-Ph led to a complex that contains three molecules of water. Kanemasa's group previously observed a decrease of asymmetric induction when the reaction is performed in the presence of molecular sieves. See, for instance: Itoh, S.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394.
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2O and DBFOX-Ph led to a complex that contains three molecules of water. Kanemasa's group previously observed a decrease of asymmetric induction when the reaction is performed in the presence of molecular sieves. See, for instance: Itoh, S.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394.
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For an example of the preparation of a chiral [1,2,4]benzo-thiadiazine-5, 5-dioxide with activity as an AMPA receptor modulator, see: Cobley, C. J.; Foucher, E.; Lecouve, J.-P.; Lennon, I. C.; Ramsdem, J. A.; Thominot, G. Tetrahedron: Asymmetry 2003, 14, 3431.
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1. CCDC 641861 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
-
1. CCDC 641861 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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60
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63849255011
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Critical NOE contacts for 54a and 54b are shown in Figure 3 below.
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Critical NOE contacts for 54a and 54b are shown in Figure 3 below.
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61
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63849112669
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The supplementary crystallographic data for 54b can be found in the Supporting Information of ref. 22.
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The supplementary crystallographic data for 54b can be found in the Supporting Information of ref. 22.
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64
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0009584878
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Hypercube Inc, Gainesville FL
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(c) HyperChem 6.02; Hypercube Inc.: Gainesville FL, 1999.
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision E.01; Gaussian Inc.: Wallingford CT, 2004.
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