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Volumn 71, Issue 21, 2006, Pages 8316-8319

A metal-free approach to the synthesis of indoline derivatives by a phenyliodine(III) bis(trifluoroacetate)-mediated amidohydroxylation reaction

Author keywords

[No Author keywords available]

Indexed keywords

AMIDOHYDROXYLATION REACTION; INDOLINE DERIVATIVES; PHENYLIODINE(III) BIS(TRIFLUOROACETATE);

EID: 33750025600     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061486q     Document Type: Article
Times cited : (123)

References (34)
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  • 2
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    • Catalytic asymmetric dihydroxylation: Discovery and development
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    • (b) Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Dihydroxylation: Discovery and Development. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 357-398.
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    • Recent advances in asymmetric dihydroxylation and aminohydroxylation
    • Ojima, I., Ed.; Wiley-VCH: New York
    • (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.
    • (2000) Catalytic Asymmetric Synthesis , pp. 399-428
    • Bolm, C.1    Hildebrand, J.P.2    Muniz, K.3
  • 5
    • 0000923203 scopus 로고
    • Trost, B. M., Fleming, L., Eds.; Pergamon: Oxford, U.K.
    • Block, E.; Schwan, A. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 4, pp 329-362.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 329-362
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  • 6
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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.
    • (1990) J. Med. Chem. , vol.33 , pp. 1929-1932
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  • 9
    • 7444269099 scopus 로고    scopus 로고
    • For palladium-catalyzed synthesis of indolines, see (a) Lira, R.; Wolfe, J. P. J. Am. Chem. Soc. 2004, 126, 13906-13907.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13906-13907
    • Lira, R.1    Wolfe, J.P.2
  • 17
    • 0036628555 scopus 로고    scopus 로고
    • 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.
    • (2002) Chem. Rev. , vol.102 , pp. 2523-12284
    • Zhdankin, V.V.1    Stang, P.J.2
  • 23
    • 4143069529 scopus 로고    scopus 로고
    • 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.
    • (2004) Tetrahedron , vol.60 , pp. 6533-6539
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  • 25
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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.
    • (1990) Chem. Lett. , pp. 581-582
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    • Moss, R. A.; Platz, M. S.; Jones, M., Jr., Eds.; Wiley-Interscience: New York
    • 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.
    • (2004) Reactive Intermediate Chemistry , pp. 594-650
    • Falvey, D.E.1
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    • note
    • Due to its labile nature, indoline 4c had also to be acetylated for a full structural identification.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.