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Volumn 70, Issue 5, 2005, Pages 1791-1795

Novel approach to 5-substituted proline derivatives using a silver-catalyzed cyclization as the key step

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSTS; ISOMERS; SILVER; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 14544296112     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0484023     Document Type: Article
Times cited : (83)

References (40)
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    • For recent entries, see: (a) Del Valle, J. R.; Goodman, M. J. Org. Chem. 2003, 68, 3923. (b) Pellegrini, N.; Schmitt, M.; Bourguignon, J.-J. Tetrahedron Lett. 2003, 44, 6779. (c) Zhang, J.; Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2003, 44, 1413. (d) Del Valle, J. R.; Goodman, M. Angew. Chem., Int. Ed. 2002, 41, 1600. (e) Xia, Q.; Ganem, B. Tetrahedron Lett. 2002, 43, 1597. (f) Flamant-Robin, C.; Wian, Q.; Chiaroni, A.; Sasaki, N. A. Tetrahedron Lett. 2002, 43, 10475. (g) Nevalainen, M.; Kauppinen, P. M.; Koskinen, A. M. P. J. Org. Chem. 2001, 66, 2061. (h) Kamenecka, T. M.; Park, Y.-J.; Lin, L. S.; Lanza, T., Jr.; Hagmann, W. K. Tetrahedron Lett. 2001, 42, 8571.
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    • For recent entries, see: (a) Del Valle, J. R.; Goodman, M. J. Org. Chem. 2003, 68, 3923. (b) Pellegrini, N.; Schmitt, M.; Bourguignon, J.-J. Tetrahedron Lett. 2003, 44, 6779. (c) Zhang, J.; Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2003, 44, 1413. (d) Del Valle, J. R.; Goodman, M. Angew. Chem., Int. Ed. 2002, 41, 1600. (e) Xia, Q.; Ganem, B. Tetrahedron Lett. 2002, 43, 1597. (f) Flamant-Robin, C.; Wian, Q.; Chiaroni, A.; Sasaki, N. A. Tetrahedron Lett. 2002, 43, 10475. (g) Nevalainen, M.; Kauppinen, P. M.; Koskinen, A. M. P. J. Org. Chem. 2001, 66, 2061. (h) Kamenecka, T. M.; Park, Y.-J.; Lin, L. S.; Lanza, T., Jr.; Hagmann, W. K. Tetrahedron Lett. 2001, 42, 8571.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 10475
    • Flamant-Robin, C.1    Wian, Q.2    Chiaroni, A.3    Sasaki, N.A.4
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    • 0035937294 scopus 로고    scopus 로고
    • For recent entries, see: (a) Del Valle, J. R.; Goodman, M. J. Org. Chem. 2003, 68, 3923. (b) Pellegrini, N.; Schmitt, M.; Bourguignon, J.-J. Tetrahedron Lett. 2003, 44, 6779. (c) Zhang, J.; Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2003, 44, 1413. (d) Del Valle, J. R.; Goodman, M. Angew. Chem., Int. Ed. 2002, 41, 1600. (e) Xia, Q.; Ganem, B. Tetrahedron Lett. 2002, 43, 1597. (f) Flamant-Robin, C.; Wian, Q.; Chiaroni, A.; Sasaki, N. A. Tetrahedron Lett. 2002, 43, 10475. (g) Nevalainen, M.; Kauppinen, P. M.; Koskinen, A. M. P. J. Org. Chem. 2001, 66, 2061. (h) Kamenecka, T. M.; Park, Y.-J.; Lin, L. S.; Lanza, T., Jr.; Hagmann, W. K. Tetrahedron Lett. 2001, 42, 8571.
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    • Nevalainen, M.1    Kauppinen, P.M.2    Koskinen, A.M.P.3
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    • For recent entries, see: (a) Del Valle, J. R.; Goodman, M. J. Org. Chem. 2003, 68, 3923. (b) Pellegrini, N.; Schmitt, M.; Bourguignon, J.-J. Tetrahedron Lett. 2003, 44, 6779. (c) Zhang, J.; Wang, W.; Xiong, C.; Hruby, V. J. Tetrahedron Lett. 2003, 44, 1413. (d) Del Valle, J. R.; Goodman, M. Angew. Chem., Int. Ed. 2002, 41, 1600. (e) Xia, Q.; Ganem, B. Tetrahedron Lett. 2002, 43, 1597. (f) Flamant-Robin, C.; Wian, Q.; Chiaroni, A.; Sasaki, N. A. Tetrahedron Lett. 2002, 43, 10475. (g) Nevalainen, M.; Kauppinen, P. M.; Koskinen, A. M. P. J. Org. Chem. 2001, 66, 2061. (h) Kamenecka, T. M.; Park, Y.-J.; Lin, L. S.; Lanza, T., Jr.; Hagmann, W. K. Tetrahedron Lett. 2001, 42, 8571.
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    • This trifunctional amino acid (2-amino-4-pentynoic acid) is commercially available but in our group also readily prepared via a chemoenzymatic procedure that has been developed in collaboration with DSM Research (Geleen, The Netherlands): (a) Wolf, L. B.; Sonke, T.; Tjen, K. C. M. F.; Kaptein, B.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2001, 343, 662. (b) Sonke, T.; Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Formaggio, F.; Toniolo, C.; Rutjes, F. P. J. T.; Schoemaker, H. E. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 2000; p 23.
    • (2001) Adv. Synth. Catal. , vol.343 , pp. 662
    • Wolf, L.B.1    Sonke, T.2    Tjen, K.C.M.F.3    Kaptein, B.4    Broxterman, Q.B.5    Schoemaker, H.E.6    Rutjes, F.P.J.T.7
  • 30
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    • Patel, R. N., Ed.; Marcel Dekker: New York
    • This trifunctional amino acid (2-amino-4-pentynoic acid) is commercially available but in our group also readily prepared via a chemoenzymatic procedure that has been developed in collaboration with DSM Research (Geleen, The Netherlands): (a) Wolf, L. B.; Sonke, T.; Tjen, K. C. M. F.; Kaptein, B.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2001, 343, 662. (b) Sonke, T.; Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Formaggio, F.; Toniolo, C.; Rutjes, F. P. J. T.; Schoemaker, H. E. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 2000; p 23.
    • (2000) Stereoselective Biocatalysis , pp. 23
    • Sonke, T.1    Kaptein, B.2    Boesten, W.H.J.3    Broxterman, Q.B.4    Kamphuis, J.5    Formaggio, F.6    Toniolo, C.7    Rutjes, F.P.J.T.8    Schoemaker, H.E.9
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    • and references therein
    • (d) Jacobi, P. A.; Liu, H. J. Org. Chem. 2000, 65, 7676 and references therein.
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    • Jacobi, P.A.1    Liu, H.2
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    • The Pd-catalyzed functionalization of propargylglycine derivatives with aromatic groups under Sonogashira-type conditions has already been described: Crisp, G. T.; Robinson, T. A. Tetrahedron 1992, 48, 3239.
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    • Crisp, G.T.1    Robinson, T.A.2


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