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Volumn 52, Issue 20, 1996, Pages 6983-6996

The palladium-catalysed vinylic substitution of vinyl triflates with β-substituted-α,β-unsaturated carbonyl compounds. An application to the synthesis of cardenolides

Author keywords

[No Author keywords available]

Indexed keywords

CARDENOLIDE;

EID: 0029869371     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00303-1     Document Type: Article
Times cited : (47)

References (39)
  • 1
    • 0002776257 scopus 로고
    • JAI Press Inc.
    • For recent reviews on the Heck reaction, see: Larock, R.C. in Advances in Metal-Organic Chemistry Vol.3, p. 97, JAI Press Inc., 1993; de Mejiere, A.; Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; Cabri, W; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
    • (1993) Advances in Metal-organic Chemistry , vol.3 , pp. 97
    • Larock, R.C.1
  • 2
    • 33748647785 scopus 로고
    • For recent reviews on the Heck reaction, see: Larock, R.C. in Advances in Metal-Organic Chemistry Vol.3, p. 97, JAI Press Inc., 1993; de Mejiere, A.; Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; Cabri, W; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2379
    • De Mejiere, A.1    Meyer, F.E.2
  • 3
    • 0038584673 scopus 로고
    • For recent reviews on the Heck reaction, see: Larock, R.C. in Advances in Metal-Organic Chemistry Vol.3, p. 97, JAI Press Inc., 1993; de Mejiere, A.; Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379; Cabri, W; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 2
    • Cabri, W.1    Candiani, I.2
  • 5
    • 0027180141 scopus 로고
    • For recent reviews on the vinylic substitution reaction of unsaturated triflates, see ref. 1 and Ritter, K. Synthesis 1993, 735; Cacchi, S. in Seminar in Organic Synthesis , p. 217, Polo Editoriale Chimico, Milano, 1993.
    • (1993) Synthesis , pp. 735
    • Ritter, K.1
  • 6
    • 0342790104 scopus 로고
    • Polo Editoriale Chimico, Milano
    • For recent reviews on the vinylic substitution reaction of unsaturated triflates, see ref. 1 and Ritter, K. Synthesis 1993, 735; Cacchi, S. in Seminar in Organic Synthesis , p. 217, Polo Editoriale Chimico, Milano, 1993.
    • (1993) Seminar in Organic Synthesis , pp. 217
    • Cacchi, S.1
  • 9
    • 33845376366 scopus 로고
    • See for example: Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Andersson, C.-M.; Hallberg, A. J. Org. Chem. 1988, 53, 2112; Fiess, B.; Cazes, B.; Gore, J. Tetrahedron Lett. 1988, 29, 4089; Cacchi, S.; Ciattini, P.G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1988, 29, 3177.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 3033
    • Scott, W.J.1    Stille, J.K.2
  • 10
    • 0345030827 scopus 로고
    • See for example: Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Andersson, C.-M.; Hallberg, A. J. Org. Chem. 1988, 53, 2112; Fiess, B.; Cazes, B.; Gore, J. Tetrahedron Lett. 1988, 29, 4089; Cacchi, S.; Ciattini, P.G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1988, 29, 3177.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5478
    • Echavarren, A.M.1    Stille, J.K.2
  • 11
    • 0001632035 scopus 로고
    • See for example: Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Andersson, C.-M.; Hallberg, A. J. Org. Chem. 1988, 53, 2112; Fiess, B.; Cazes, B.; Gore, J. Tetrahedron Lett. 1988, 29, 4089; Cacchi, S.; Ciattini, P.G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1988, 29, 3177.
    • (1988) J. Org. Chem. , vol.53 , pp. 2112
    • Andersson, C.-M.1    Hallberg, A.2
  • 12
    • 0001588021 scopus 로고
    • See for example: Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Andersson, C.-M.; Hallberg, A. J. Org. Chem. 1988, 53, 2112; Fiess, B.; Cazes, B.; Gore, J. Tetrahedron Lett. 1988, 29, 4089; Cacchi, S.; Ciattini, P.G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1988, 29, 3177.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4089
    • Fiess, B.1    Cazes, B.2    Gore, J.3
  • 13
    • 0343224655 scopus 로고
    • See for example: Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033; Echavarren, A.M.; Stille, J.K. J. Am. Chem. Soc. 1987, 109, 5478; Andersson, C.-M.; Hallberg, A. J. Org. Chem. 1988, 53, 2112; Fiess, B.; Cazes, B.; Gore, J. Tetrahedron Lett. 1988, 29, 4089; Cacchi, S.; Ciattini, P.G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1988, 29, 3177.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 3177
    • Cacchi, S.1    Ciattini, P.G.2    Morera, E.3    Ortar, G.4
  • 15
    • 46549101525 scopus 로고
    • Jeffery, T. J. Chem. Soc., Chem. Comm. 1984, 1287; Jeffery, T. Tetrahedron Lett. 1985, 26, 2667.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2667
    • Jeffery, T.1
  • 16
    • 0000151617 scopus 로고
    • Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M.A. Organometallics 1995, 14, 1818; Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M.A.; Meyer, G. Organometallics 1995, 14, 5005; Amatore, C.; Jutand, A.; M'Barki, M.A. Organometallics 1992, 11, 3009. See also Amatore, C.; Blart, E.; Genêt, G.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829.
    • (1995) Organometallics , vol.14 , pp. 1818
    • Amatore, C.1    Carré, E.2    Jutand, A.3    M'Barki, M.A.4
  • 17
    • 85030196106 scopus 로고
    • Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M.A. Organometallics 1995, 14, 1818; Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M.A.; Meyer, G. Organometallics 1995, 14, 5005; Amatore, C.; Jutand, A.; M'Barki, M.A. Organometallics 1992, 11, 3009. See also Amatore, C.; Blart, E.; Genêt, G.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829.
    • (1995) Organometallics , vol.14 , pp. 5005
    • Amatore, C.1    Carré, E.2    Jutand, A.3    M'Barki, M.A.4    Meyer, G.5
  • 18
    • 0000852316 scopus 로고
    • Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M.A. Organometallics 1995, 14, 1818; Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M.A.; Meyer, G. Organometallics 1995, 14, 5005; Amatore, C.; Jutand, A.; M'Barki, M.A. Organometallics 1992, 11, 3009. See also Amatore, C.; Blart, E.; Genêt, G.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829.
    • (1992) Organometallics , vol.11 , pp. 3009
    • Amatore, C.1    Jutand, A.2    M'Barki, M.A.3
  • 19
    • 33751155540 scopus 로고
    • Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M.A. Organometallics 1995, 14, 1818; Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M.A.; Meyer, G. Organometallics 1995, 14, 5005; Amatore, C.; Jutand, A.; M'Barki, M.A. Organometallics 1992, 11, 3009. See also Amatore, C.; Blart, E.; Genêt, G.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829.
    • (1995) J. Org. Chem. , vol.60 , pp. 6829
    • Amatore, C.1    Blart, E.2    Genêt, G.P.3    Jutand, A.4    Lemaire-Audoire, S.5    Savignac, M.6
  • 21
    • 85030189149 scopus 로고    scopus 로고
    • note
    • The relevant NOE effects for the determination of the regio- and stereochemistry of 3q and 3r, presented by arrows, are as follows: (formula presented) The same protons generated clear off-diagonal contours in NOESY spectra.
  • 23
    • 84994929046 scopus 로고
    • Stang, P.J.; Treptow, W. Synthesis 1980, 283; Stang, P.J.; Hanack, M.; Subramanian, L.R. Synthesis 1982, 85; Cacchi, S.; Morera, E.; Ortar, G. Org. Synth. 1990, 68, 138.
    • (1980) Synthesis , pp. 283
    • Stang, P.J.1    Treptow, W.2
  • 24
    • 85007950754 scopus 로고
    • Stang, P.J.; Treptow, W. Synthesis 1980, 283; Stang, P.J.; Hanack, M.; Subramanian, L.R. Synthesis 1982, 85; Cacchi, S.; Morera, E.; Ortar, G. Org. Synth. 1990, 68, 138.
    • (1982) Synthesis , pp. 85
    • Stang, P.J.1    Hanack, M.2    Subramanian, L.R.3
  • 25
    • 0001088215 scopus 로고
    • Stang, P.J.; Treptow, W. Synthesis 1980, 283; Stang, P.J.; Hanack, M.; Subramanian, L.R. Synthesis 1982, 85; Cacchi, S.; Morera, E.; Ortar, G. Org. Synth. 1990, 68, 138.
    • (1990) Org. Synth. , vol.68 , pp. 138
    • Cacchi, S.1    Morera, E.2    Ortar, G.3
  • 26
    • 33751157390 scopus 로고
    • Leading references: Larock, R.C.; Wang, Y.; Lu, Y.-de; Russell, C.E. J. Org. Chem. 1994, 59, 8107; Larock, R.C.; Lu, Y.-de; Bain, A.C. J. Org. Chem. 1991, 56, 4589; Larock, R.C.; Leung, W.-Y. J. Org. Chem. 1990, 55, 6244.
    • (1994) J. Org. Chem. , vol.59 , pp. 8107
    • Larock, R.C.1    Wang, Y.2    Lu, Y.-De.3    Russell, C.E.4
  • 27
    • 0000842555 scopus 로고
    • Leading references: Larock, R.C.; Wang, Y.; Lu, Y.-de; Russell, C.E. J. Org. Chem. 1994, 59, 8107; Larock, R.C.; Lu, Y.-de; Bain, A.C. J. Org. Chem. 1991, 56, 4589; Larock, R.C.; Leung, W.-Y. J. Org. Chem. 1990, 55, 6244.
    • (1991) J. Org. Chem. , vol.56 , pp. 4589
    • Larock, R.C.1    Lu, Y.-De.2    Bain, A.C.3
  • 28
    • 0000742207 scopus 로고
    • Leading references: Larock, R.C.; Wang, Y.; Lu, Y.-de; Russell, C.E. J. Org. Chem. 1994, 59, 8107; Larock, R.C.; Lu, Y.-de; Bain, A.C. J. Org. Chem. 1991, 56, 4589; Larock, R.C.; Leung, W.-Y. J. Org. Chem. 1990, 55, 6244.
    • (1990) J. Org. Chem. , vol.55 , pp. 6244
    • Larock, R.C.1    Leung, W.-Y.2
  • 29
    • 85030189712 scopus 로고    scopus 로고
    • note
    • 5
  • 31
    • 85030187584 scopus 로고    scopus 로고
    • note
    • 18 in the presence of tertiary amines have been used to prepare hydrovinylation derivatives from aryl halides and β-substituted-α,β-unsaturated carbonyl compounds.
  • 34
    • 0000933730 scopus 로고
    • For the use of tertiary amines as promoters of hydroarylarion reactions, see: ref. 17; Stokkler, G.E. Tetrahedron Lett. 1987, 28, 3179; Friestad, G.K.; Branchaud, B.P. Tetrahedron Lett. 1995, 36, 7047.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3179
    • Stokkler, G.E.1
  • 35
    • 0029121970 scopus 로고
    • For the use of tertiary amines as promoters of hydroarylarion reactions, see: ref. 17; Stokkler, G.E. Tetrahedron Lett. 1987, 28, 3179; Friestad, G.K.; Branchaud, B.P. Tetrahedron Lett. 1995, 36, 7047.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7047
    • Friestad, G.K.1    Branchaud, B.P.2


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