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Ojima, I., Ed.; Wiley-VCH: New York
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Ojima, I., Ed.; Wiley-VCH: New York
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(c) Bolm, C.; Hildebrand, J. P.; Muniz, K. Recent Advances in Asymmetric Dihydroxylation and Aminohydroxylation. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 399-428.
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Hildebrand, J.P.2
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2-Methylindoline derivatives constitute a structural class of heterocycles from which several drugs have emerged, including antineoplastic sulfonamides, 5-hydroxytryptamine receptor antagonists (5-HT3), and muscarine receptor agonists and antagonists. See for example (a) Bermudez, J.; Dabbs, S.; Joiner, K. A.; King, F. D. J. Med. Chem. 1990, 33, 1929-1932.
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For palladium-catalyzed synthesis of indolines, see (a) Lira, R.; Wolfe, J. P. J. Am. Chem. Soc. 2004, 126, 13906-13907.
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(g) Gleave, D. M.; Brickner, S. J.; Manninen, P. R.; Allwine, D. A.; Lovasz, K. D.; Rohrer, D. C.; Tucker, J. A.; Zurenko, G. E.; Ford, C. W. Bioorg. Med. Chem. Lett. 1998, 8, 1231-1236.
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For recent reviews on the synthetic applications of polyvalent iodine reagents, see (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2284.
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For some other contributions by our group on the synthesis of other N-containing heterocycles by employing this PIFA-promoted olefin amidohydroxylation, see (a) Serna, S.; Tellitu, I.; Domínguez, E.; Moreno, I.; SanMartin, R. Tetrahedron 2004, 60, 6533-6539.
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(b) Serna, S.; Tellitu, I.; Domínguez, E.; Moreno, I.; SanMartin, R. Tetrahedron Lett. 2003, 44, 3483-3486.
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Moreno, I.4
Sanmartin, R.5
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The hypervalent iodine reagent PIFA has been reported to generate N-acylnitrenium ions from adequately substituted amides. See for example (a) Kikugawa, Y.; Kawase, M. Chem. Lett. 1990, 581-582.
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Moss, R. A.; Platz, M. S.; Jones, M., Jr., Eds.; Wiley-Interscience: New York
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Unless a nitrenium ion is stabilized by a proper neighboring group, such as an aryl or alkoxy group, its existence as a reaction intermediate is quite fleeting. Thus, the selection of an adequate N-substituent is of key importance. For some reviews on nitrenium intermediates, see (a) Falvey, D. E. In Reactive Intermediate Chemistry Moss, R. A.; Platz, M. S.; Jones, M., Jr., Eds.; Wiley-Interscience: New York, 2004; pp 594-650.
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Reactive Intermediate Chemistry
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Falvey, D.E.1
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note
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Due to its labile nature, indoline 4c had also to be acetylated for a full structural identification.
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