Amino Acid Derivatives by Multicomponent Reactions

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 16, 1997, Pages 1700-1702

  Dyker, Gerald ^a  

^a Fachbereich 6   (Germany)

Author keywords

Amino acids; Carbonylations; Homogeneous catalysis; Multicomponent reactions; Palladium

Indexed keywords

EID: 0030821811     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199717001     Document Type: Review

References (60)

1. Current examples of the synthesis of α-amino acids: a) J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1990, pp. 300-305; b) R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650; c) U. Kazmaier, Liebigs Ann./Recueil 1997, 285-295; d) M. Braun, K. Opdenbusch, ibid. 1997, 141-154; e) L. S. Hegedus, Acc. Chem. Res. 1995, 28, 299-305; f) D. Enders, R. Funk, M. Klatt, O. Raabe, E. R. Hovestreydt, Angev. Chem. 1993, 105, 418-420; Angew. Chem. Int. Ed. Engl. 1993, 32, 418-420.
2. Current examples of the synthesis of α-amino acids: a) J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1990, pp. 300-305; b) R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650; c) U. Kazmaier, Liebigs Ann./Recueil 1997, 285-295; d) M. Braun, K. Opdenbusch, ibid. 1997, 141-154; e) L. S. Hegedus, Acc. Chem. Res. 1995, 28, 299-305; f) D. Enders, R. Funk, M. Klatt, O. Raabe, E. R. Hovestreydt, Angev. Chem. 1993, 105, 418-420; Angew. Chem. Int. Ed. Engl. 1993, 32, 418-420.
3. Current examples of the synthesis of α-amino acids: a) J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1990, pp. 300-305; b) R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650; c) U. Kazmaier, Liebigs Ann./Recueil 1997, 285-295; d) M. Braun, K. Opdenbusch, ibid. 1997, 141-154; e) L. S. Hegedus, Acc. Chem. Res. 1995, 28, 299-305; f) D. Enders, R. Funk, M. Klatt, O. Raabe, E. R. Hovestreydt, Angev. Chem. 1993, 105, 418-420; Angew. Chem. Int. Ed. Engl. 1993, 32, 418-420.
4. Current examples of the synthesis of α-amino acids: a) J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1990, pp. 300-305; b) R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650; c) U. Kazmaier, Liebigs Ann./Recueil 1997, 285-295; d) M. Braun, K. Opdenbusch, ibid. 1997, 141-154; e) L. S. Hegedus, Acc. Chem. Res. 1995, 28, 299-305; f) D. Enders, R. Funk, M. Klatt, O. Raabe, E. R. Hovestreydt, Angev. Chem. 1993, 105, 418-420; Angew. Chem. Int. Ed. Engl. 1993, 32, 418-420.
5. Current examples of the synthesis of α-amino acids: a) J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1990, pp. 300-305; b) R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650; c) U. Kazmaier, Liebigs Ann./Recueil 1997, 285-295; d) M. Braun, K. Opdenbusch, ibid. 1997, 141-154; e) L. S. Hegedus, Acc. Chem. Res. 1995, 28, 299-305; f) D. Enders, R. Funk, M. Klatt, O. Raabe, E. R. Hovestreydt, Angev. Chem. 1993, 105, 418-420; Angew. Chem. Int. Ed. Engl. 1993, 32, 418-420.
6. Current examples of the synthesis of α-amino acids: a) J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1990, pp. 300-305; b) R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650; c) U. Kazmaier, Liebigs Ann./Recueil 1997, 285-295; d) M. Braun, K. Opdenbusch, ibid. 1997, 141-154; e) L. S. Hegedus, Acc. Chem. Res. 1995, 28, 299-305; f) D. Enders, R. Funk, M. Klatt, O. Raabe, E. R. Hovestreydt, Angev. Chem. 1993, 105, 418-420; Angew. Chem. Int. Ed. Engl. 1993, 32, 418-420.
7. Current examples of the synthesis of α-amino acids: a) J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1990, pp. 300-305; b) R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650; c) U. Kazmaier, Liebigs Ann./Recueil 1997, 285-295; d) M. Braun, K. Opdenbusch, ibid. 1997, 141-154; e) L. S. Hegedus, Acc. Chem. Res. 1995, 28, 299-305; f) D. Enders, R. Funk, M. Klatt, O. Raabe, E. R. Hovestreydt, Angev. Chem. 1993, 105, 418-420; Angew. Chem. Int. Ed. Engl. 1993, 32, 418-420.
8. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
9. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
10. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
11. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
12. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
13. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
14. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
15. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
16. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
17. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
18. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
19. Current examples of the synthesis of β-amino acids: a) D. Enders, J. Wiedemann, Liebigs Ann./Recueil 1997, 699-706; b) J. Voigt, M. Noltemeyer, O. Reiser, Synlett 1997, 202-204; c) H. Kunz, A. Burgard, D. Schanzenbach, Angew. Chem. 1997, 109, 394-396; Angew. Chem. Int. Ed. Engl. 1997, 36, 386-387; d) G. Cardillo, S. Casolari, L. Gentilucci, C. Tomasini, ibid. 1996, 108, 1939-1941 and 1996, 35, 1848-1849; e) J. Podlech, D. Seebach, ibid. 1995, 107, 507-509 and 1995, 34, 471-472; f) Liebigs Ann. 1995, 1217-1228; g) P. Gmeiner, E. Hummel, C. Haubmann, ibid. 1995, 1987-1992; h) J. Escalante, E. Juaristi, Tetrahedron Lett. 1995, 36, 4397-4400; i) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
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53. Further examples of amino acid syntheses starting with glyoxylic acid derivatives; a) P. Münster, W. Steglich, Synthesis 1987, 223-225; b) M. J. O'Donnell, W. D. Bennett, Tetrahedron 1988, 44, 5389-5401; c) E. C. Roos, M. C. Lopez, M. A. Brook, H. Hiemstra, W. N. Speckamp, B. Kaptein, J. Kamphuis, H. E. Schoemaker, J. Org. Chem. 1993, 58, 3259-3268.
54. Further examples of amino acid syntheses starting with glyoxylic acid derivatives; a) P. Münster, W. Steglich, Synthesis 1987, 223-225; b) M. J. O'Donnell, W. D. Bennett, Tetrahedron 1988, 44, 5389-5401; c) E. C. Roos, M. C. Lopez, M. A. Brook, H. Hiemstra, W. N. Speckamp, B. Kaptein, J. Kamphuis, H. E. Schoemaker, J. Org. Chem. 1993, 58, 3259-3268.
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