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Volumn 5, Issue 24, 2003, Pages 4749-4752

Palladium-Catalyzed Amidation of Enol Triflates: A New Synthesis of Enamides

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; CARBAMIC ACID DERIVATIVE; PALLADIUM; SULFONAMIDE; TRIFLUOROMETHANESULFONIC ACID;

EID: 0347411032     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035959g     Document Type: Article
Times cited : (144)

References (28)
  • 15
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    • Willis, M. C.; Brace, G. N. Tetrahedron Lett. 2002, 43, 9085. See also Hicks, F. A.; Brookhardt, M. Org. Lett. 2000, 2, 219.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 9085
    • Willis, M.C.1    Brace, G.N.2
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    • Willis, M. C.; Brace, G. N. Tetrahedron Lett. 2002, 43, 9085. See also Hicks, F. A.; Brookhardt, M. Org. Lett. 2000, 2, 219.
    • (2000) Org. Lett. , vol.2 , pp. 219
    • Hicks, F.A.1    Brookhardt, M.2
  • 18
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    • For stereocontrolled synthesis of 1,2-disubstituted enamides, see: (a) Furstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955. (b) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407 and references therein. For stereoselective preparation of trisubstituted enamides, see: Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67 and references therein.
    • (2001) Org. Lett. , vol.3 , pp. 3955
    • Furstner, A.1    Brehm, C.2    Cancho-Grande, Y.3
  • 19
    • 0034628240 scopus 로고    scopus 로고
    • and references therein
    • For stereocontrolled synthesis of 1,2-disubstituted enamides, see: (a) Furstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955. (b) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407 and references therein. For stereoselective preparation of trisubstituted enamides, see: Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67 and references therein.
    • (2000) Org. Lett. , vol.2 , pp. 407
    • Snider, B.B.1    Song, F.2
  • 20
    • 0037884003 scopus 로고    scopus 로고
    • and references therein
    • For stereocontrolled synthesis of 1,2-disubstituted enamides, see: (a) Furstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955. (b) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407 and references therein. For stereoselective preparation of trisubstituted enamides, see: Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67 and references therein.
    • (2003) Org. Lett. , vol.5 , pp. 67
    • Tanaka, R.1    Hirano, S.2    Urabe, H.3    Sato, F.4
  • 21
    • 0142106421 scopus 로고    scopus 로고
    • For copper-catalyzed amidations of vinyl halides, see: (a) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L Org. Lett. 2003, 5, 3667. (b) Shen, R.; Porco, J. A. Jr. Org. Lett. 2000, 2, 1333. (c) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443. For a palladium-catalyzed intramolecular reaction, see: Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111.
    • (2003) Org. Lett. , vol.5 , pp. 3667
    • Jiang, L.1    Job, G.E.2    Klapars, A.3    Buchwald, S.L.4
  • 22
    • 0001572533 scopus 로고    scopus 로고
    • For copper-catalyzed amidations of vinyl halides, see: (a) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L Org. Lett. 2003, 5, 3667. (b) Shen, R.; Porco, J. A. Jr. Org. Lett. 2000, 2, 1333. (c) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443. For a palladium-catalyzed intramolecular reaction, see: Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111.
    • (2000) Org. Lett. , vol.2 , pp. 1333
    • Shen, R.1    Porco Jr., J.A.2
  • 23
    • 0002251888 scopus 로고
    • For copper-catalyzed amidations of vinyl halides, see: (a) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L Org. Lett. 2003, 5, 3667. (b) Shen, R.; Porco, J. A. Jr. Org. Lett. 2000, 2, 1333. (c) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443. For a palladium-catalyzed intramolecular reaction, see: Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111.
    • (1991) Chem. Lett. , pp. 1443
    • Ogawa, T.1    Kiji, T.2    Hayami, K.3    Suzuki, H.4
  • 24
    • 0036134301 scopus 로고    scopus 로고
    • For copper-catalyzed amidations of vinyl halides, see: (a) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L Org. Lett. 2003, 5, 3667. (b) Shen, R.; Porco, J. A. Jr. Org. Lett. 2000, 2, 1333. (c) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443. For a palladium-catalyzed intramolecular reaction, see: Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 111
    • Kozawa, Y.1    Mori, M.2
  • 26
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    • note
    • 13C, IR, and HRMS and/or elemental analysis.
  • 27
    • 0347148563 scopus 로고    scopus 로고
    • note
    • +) theory 258.1858, measured 258.1851.
  • 28
    • 0347148564 scopus 로고    scopus 로고
    • note
    • While a conjugate addition/elimination pathway could operate for this enol triflate, we feel that this is unlikely due to the lack of reactivity in the absence of palladium (<5% conversion after 24 h). We thank a referee for alerting us to this possibility.


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