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Volumn 43, Issue 50, 2002, Pages 9085-9088

Palladium catalysed enamine synthesis from vinyl triflates

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBONIC ACID DERIVATIVE; CHEMICAL COMPOUND; ENAMINE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID; VINYL DERIVATIVE;

EID: 0037049225     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02249-9     Document Type: Article
Times cited : (69)

References (21)
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    • Trost, B. M.; Fleming, I. Eds.; Oxford: Pergamon
    • For general reviews on enamine chemistry, see: (a) Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Oxford: Pergamon, 1991; (b) Cook, A. G., Ed., Enamines; New York: Marcel Decker, 1988.
    • (1991) Comprehensive Organic Synthesis
    • Whitesell, J.K.1
  • 2
    • 0004215714 scopus 로고
    • New York: Marcel Decker
    • For general reviews on enamine chemistry, see: (a) Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Oxford: Pergamon, 1991; (b) Cook, A. G., Ed., Enamines; New York: Marcel Decker, 1988.
    • (1988) Enamines
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  • 3
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    • For example: (a) Aznar, F.; Valdés, C.; Cabal, M.-P. Tetrahedron Lett. 2000, 41, 5683; (b) Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7111.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 5683
    • Aznar, F.1    Valdés, C.2    Cabal, M.-P.3
  • 4
    • 0030756775 scopus 로고    scopus 로고
    • For example: (a) Aznar, F.; Valdés, C.; Cabal, M.-P. Tetrahedron Lett. 2000, 41, 5683; (b) Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7111.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7111
    • Hird, N.W.1    Irie, K.2    Nagai, K.3
  • 8
    • 0027180141 scopus 로고
    • For a review on the uses and preparations of triflate derivatives, see: Ritter, K. Synthesis 1993, 735.
    • (1993) Synthesis , pp. 735
    • Ritter, K.1
  • 9
    • 0004136578 scopus 로고    scopus 로고
    • Ricci, A. Ed.; Weinheim: Wiley-VCH
    • For reviews, see: (a) Hartwig, J. F. In Modern Amination Methods; Ricci, A. Ed.; Weinheim: Wiley-VCH, 2000; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805; (c) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
    • (2000) Modern Amination Methods
    • Hartwig, J.F.1
  • 10
    • 0001038733 scopus 로고    scopus 로고
    • For reviews, see: (a) Hartwig, J. F. In Modern Amination Methods; Ricci, A. Ed.; Weinheim: Wiley-VCH, 2000; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805; (c) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 805
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  • 11
    • 0000157513 scopus 로고    scopus 로고
    • For reviews, see: (a) Hartwig, J. F. In Modern Amination Methods; Ricci, A. Ed.; Weinheim: Wiley-VCH, 2000; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805; (c) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
    • (2002) Top. Curr. Chem. , vol.219 , pp. 131
    • Muci, A.R.1    Buchwald, S.L.2
  • 12
    • 0036134301 scopus 로고    scopus 로고
    • During the course of this study an example of an intramolecular palladium catalysed coupling between a vinyl bromide and an amide was reported; Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111; an example of the intermolecular palladium catalysed coupling of vinyl bromides and azoles has also recently appeared: Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 111
    • Kozawa, Y.1    Mori, M.2
  • 13
    • 0002261207 scopus 로고    scopus 로고
    • During the course of this study an example of an intramolecular palladium catalysed coupling between a vinyl bromide and an amide was reported; Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111; an example of the intermolecular palladium catalysed coupling of vinyl bromides and azoles has also recently appeared: Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623.
    • (2002) Org. Lett. , vol.4 , pp. 623
    • Lebedev, A.Y.1    Izmer, V.V.2    Kazyul'kin, D.N.3    Beletskaya, I.P.4    Voskoboynikov, A.Z.5
  • 18
    • 0011187786 scopus 로고    scopus 로고
    • Starting triflate recovered in 93% yield.
    • Starting triflate recovered in 93% yield.
  • 19
    • 0011254887 scopus 로고    scopus 로고
    • 1H NMR spectroscopy for determination of the percentage conversion to product, or taken immediately into the next reaction.
    • 1H NMR spectroscopy for determination of the percentage conversion to product, or taken immediately into the next reaction.
  • 20
    • 0011248627 scopus 로고    scopus 로고
    • note
    • 3, 300 MHz) 1.62-1.79 (2H, m), 1.85-2.08 (2H, m), 2.41-2.55 (2H, m), 2.56-2.68 (2H, m), 2.69-2.86 (2H, m), 3.73 (4H, t, J 3.9 Hz) 3.75-3.83 (1H, m), 7.00-7.09 (1H, m), 7.09-7.21 (2H, m), 7.70 (1H, d, J 6.6 Hz).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.