A Concise β-Lactam Route to Short Peptide Segments Containing β,β-Disubstituted β-Amino Acids

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2469-2474

  Palomo, Claudio ^a   Oiarbide, Mikel ^a   Bindi, Simona ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001448817     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9712862     Document Type: Article

References (66)

1. For comprehensive reviews, see: (a) Degrade, W. F. Adv. Protein Chem. 1988, 39, 51. (b) Toniolo, C. Int. Pept. Protein Res. 1990, 35, 287. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (d) Liskamp, R. M. J. Recuil. Trav. Chim. Pays. Bass. 1994, 113, 1. (e) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
2. For comprehensive reviews, see: (a) Degrade, W. F. Adv. Protein Chem. 1988, 39, 51. (b) Toniolo, C. Int. Pept. Protein Res. 1990, 35, 287. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (d) Liskamp, R. M. J. Recuil. Trav. Chim. Pays. Bass. 1994, 113, 1. (e) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
3. For comprehensive reviews, see: (a) Degrade, W. F. Adv. Protein Chem. 1988, 39, 51. (b) Toniolo, C. Int. Pept. Protein Res. 1990, 35, 287. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (d) Liskamp, R. M. J. Recuil. Trav. Chim. Pays. Bass. 1994, 113, 1. (e) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
4. For comprehensive reviews, see: (a) Degrade, W. F. Adv. Protein Chem. 1988, 39, 51. (b) Toniolo, C. Int. Pept. Protein Res. 1990, 35, 287. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (d) Liskamp, R. M. J. Recuil. Trav. Chim. Pays. Bass. 1994, 113, 1. (e) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
5. For comprehensive reviews, see: (a) Degrade, W. F. Adv. Protein Chem. 1988, 39, 51. (b) Toniolo, C. Int. Pept. Protein Res. 1990, 35, 287. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244. (d) Liskamp, R. M. J. Recuil. Trav. Chim. Pays. Bass. 1994, 113, 1. (e) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699.
6. For some representative examples, see: (a) Toniolo, C. CRC Crit. Rev. Biochem. 1980, 5, 1. (b) Mutter, M. Angew. Chem. 1985, 97, 639. (c) Obrecht, D.; Spiegler, C.; Schoönholzer, P.; Müller, K.; Heimgartner, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666.
7. For some representative examples, see: (a) Toniolo, C. CRC Crit. Rev. Biochem. 1980, 5, 1. (b) Mutter, M. Angew. Chem. 1985, 97, 639. (c) Obrecht, D.; Spiegler, C.; Schoönholzer, P.; Müller, K.; Heimgartner, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666.
8. For some representative examples, see: (a) Toniolo, C. CRC Crit. Rev. Biochem. 1980, 5, 1. (b) Mutter, M. Angew. Chem. 1985, 97, 639. (c) Obrecht, D.; Spiegler, C.; Schoönholzer, P.; Müller, K.; Heimgartner, H.; Stierli, F. Helv. Chim. Acta 1992, 75, 1666.
9. For some representative examples, see: (a) Wipf, P.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 258. (b) Wipf, P.; Kunz, R. W.; Prewo, R.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 268. (c) Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563. (d) Obrecht, D.; Karajrannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (e) Obrecht, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Muller, K. Helv. Chim. Acta 1995, 78, 1567, (f) Obrecht, D.; Bohdal, U.; Lehmann, C.; Schönholzer, P.; Müller, K. Tetrahedron 1995, 51, 10883. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315.
10. For some representative examples, see: (a) Wipf, P.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 258. (b) Wipf, P.; Kunz, R. W.; Prewo, R.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 268. (c) Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563. (d) Obrecht, D.; Karajrannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (e) Obrecht, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Muller, K. Helv. Chim. Acta 1995, 78, 1567, (f) Obrecht, D.; Bohdal, U.; Lehmann, C.; Schönholzer, P.; Müller, K. Tetrahedron 1995, 51, 10883. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315.
11. For some representative examples, see: (a) Wipf, P.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 258. (b) Wipf, P.; Kunz, R. W.; Prewo, R.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 268. (c) Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563. (d) Obrecht, D.; Karajrannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (e) Obrecht, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Muller, K. Helv. Chim. Acta 1995, 78, 1567, (f) Obrecht, D.; Bohdal, U.; Lehmann, C.; Schönholzer, P.; Müller, K. Tetrahedron 1995, 51, 10883. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315.
12. For some representative examples, see: (a) Wipf, P.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 258. (b) Wipf, P.; Kunz, R. W.; Prewo, R.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 268. (c) Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563. (d) Obrecht, D.; Karajrannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (e) Obrecht, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Muller, K. Helv. Chim. Acta 1995, 78, 1567, (f) Obrecht, D.; Bohdal, U.; Lehmann, C.; Schönholzer, P.; Müller, K. Tetrahedron 1995, 51, 10883. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315.
13. For some representative examples, see: (a) Wipf, P.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 258. (b) Wipf, P.; Kunz, R. W.; Prewo, R.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 268. (c) Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563. (d) Obrecht, D.; Karajrannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (e) Obrecht, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Muller, K. Helv. Chim. Acta 1995, 78, 1567, (f) Obrecht, D.; Bohdal, U.; Lehmann, C.; Schönholzer, P.; Müller, K. Tetrahedron 1995, 51, 10883. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315.
14. For some representative examples, see: (a) Wipf, P.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 258. (b) Wipf, P.; Kunz, R. W.; Prewo, R.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 268. (c) Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563. (d) Obrecht, D.; Karajrannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (e) Obrecht, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Muller, K. Helv. Chim. Acta 1995, 78, 1567, (f) Obrecht, D.; Bohdal, U.; Lehmann, C.; Schönholzer, P.; Müller, K. Tetrahedron 1995, 51, 10883. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315.
15. For some representative examples, see: (a) Wipf, P.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 258. (b) Wipf, P.; Kunz, R. W.; Prewo, R.; Heimgartner, H. Helv. Chim. Acta 1988, 71, 268. (c) Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563. (d) Obrecht, D.; Karajrannis, H.; Lehmann, C.; Schönholzer, P.; Spiegler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 703. (e) Obrecht, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Muller, K. Helv. Chim. Acta 1995, 78, 1567, (f) Obrecht, D.; Bohdal, U.; Lehmann, C.; Schönholzer, P.; Müller, K. Tetrahedron 1995, 51, 10883. (g) Obrecht, D.; Abrecht, C.; Altorfer, M.; Bohdal, U.; Grieder, A.; Kleber, M.; Pfyffer, P.; Müller, K. Helv. Chim. Acta 1996, 79, 1315.
16. Hruby, V. J. In Perspectives in Peptide Chemistry; Eberle, A., Geiger, R., Wielland, T., Eds.; Karger: Basel, 1981, p 207.
17. For more information on this subject, see: (a) ref 1. (b) Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249. (c) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238.
18. For more information on this subject, see: (a) ref 1. (b) Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249. (c) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238.
19. For more information on this subject, see: (a) ref 1. (b) Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249. (c) Heimgartner, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 238.
20. For some examples documenting these aspects, see: (a) Griffith, O. W. Annu. Rev. Biochem. 1986, 55, 855. (b) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyawa, H.; Kiso, Y. J. Chem. Soc.; Chem. Commun. 1989, 1678. (c) Rodríguez, M.; Fulcrand, P.; Laur, J.; Aumelas, A.; Ball, J. P.; Martínez, J. J. Med. Chem. 1989, 32, 522. (d) Stachowiak, K.; Khosla, M. C.; Plucinska, K.; Khairallah, P. A.; Bumpus, F. M. J. Med. Chem. 1979, 22, 1128. (e) Mierke, D. F.; Nössner, G.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 35, 35. (f) Yamazaki, T.; Probstl, A.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 37, 364. (g) Huang, Z.; Probstl, A.; Spencer, J. R.; Yamazaki, T.; Goodman, M. Int. J. Pept. Protein Res. 1993, 42, 352.
21. For some examples documenting these aspects, see: (a) Griffith, O. W. Annu. Rev. Biochem. 1986, 55, 855. (b) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyawa, H.; Kiso, Y. J. Chem. Soc.; Chem. Commun. 1989, 1678. (c) Rodríguez, M.; Fulcrand, P.; Laur, J.; Aumelas, A.; Ball, J. P.; Martínez, J. J. Med. Chem. 1989, 32, 522. (d) Stachowiak, K.; Khosla, M. C.; Plucinska, K.; Khairallah, P. A.; Bumpus, F. M. J. Med. Chem. 1979, 22, 1128. (e) Mierke, D. F.; Nössner, G.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 35, 35. (f) Yamazaki, T.; Probstl, A.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 37, 364. (g) Huang, Z.; Probstl, A.; Spencer, J. R.; Yamazaki, T.; Goodman, M. Int. J. Pept. Protein Res. 1993, 42, 352.
22. For some examples documenting these aspects, see: (a) Griffith, O. W. Annu. Rev. Biochem. 1986, 55, 855. (b) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyawa, H.; Kiso, Y. J. Chem. Soc.; Chem. Commun. 1989, 1678. (c) Rodríguez, M.; Fulcrand, P.; Laur, J.; Aumelas, A.; Ball, J. P.; Martínez, J. J. Med. Chem. 1989, 32, 522. (d) Stachowiak, K.; Khosla, M. C.; Plucinska, K.; Khairallah, P. A.; Bumpus, F. M. J. Med. Chem. 1979, 22, 1128. (e) Mierke, D. F.; Nössner, G.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 35, 35. (f) Yamazaki, T.; Probstl, A.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 37, 364. (g) Huang, Z.; Probstl, A.; Spencer, J. R.; Yamazaki, T.; Goodman, M. Int. J. Pept. Protein Res. 1993, 42, 352.
23. For some examples documenting these aspects, see: (a) Griffith, O. W. Annu. Rev. Biochem. 1986, 55, 855. (b) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyawa, H.; Kiso, Y. J. Chem. Soc.; Chem. Commun. 1989, 1678. (c) Rodríguez, M.; Fulcrand, P.; Laur, J.; Aumelas, A.; Ball, J. P.; Martínez, J. J. Med. Chem. 1989, 32, 522. (d) Stachowiak, K.; Khosla, M. C.; Plucinska, K.; Khairallah, P. A.; Bumpus, F. M. J. Med. Chem. 1979, 22, 1128. (e) Mierke, D. F.; Nössner, G.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 35, 35. (f) Yamazaki, T.; Probstl, A.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 37, 364. (g) Huang, Z.; Probstl, A.; Spencer, J. R.; Yamazaki, T.; Goodman, M. Int. J. Pept. Protein Res. 1993, 42, 352.
24. For some examples documenting these aspects, see: (a) Griffith, O. W. Annu. Rev. Biochem. 1986, 55, 855. (b) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyawa, H.; Kiso, Y. J. Chem. Soc.; Chem. Commun. 1989, 1678. (c) Rodríguez, M.; Fulcrand, P.; Laur, J.; Aumelas, A.; Ball, J. P.; Martínez, J. J. Med. Chem. 1989, 32, 522. (d) Stachowiak, K.; Khosla, M. C.; Plucinska, K.; Khairallah, P. A.; Bumpus, F. M. J. Med. Chem. 1979, 22, 1128. (e) Mierke, D. F.; Nössner, G.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 35, 35. (f) Yamazaki, T.; Probstl, A.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 37, 364. (g) Huang, Z.; Probstl, A.; Spencer, J. R.; Yamazaki, T.; Goodman, M. Int. J. Pept. Protein Res. 1993, 42, 352.
25. For some examples documenting these aspects, see: (a) Griffith, O. W. Annu. Rev. Biochem. 1986, 55, 855. (b) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyawa, H.; Kiso, Y. J. Chem. Soc.; Chem. Commun. 1989, 1678. (c) Rodríguez, M.; Fulcrand, P.; Laur, J.; Aumelas, A.; Ball, J. P.; Martínez, J. J. Med. Chem. 1989, 32, 522. (d) Stachowiak, K.; Khosla, M. C.; Plucinska, K.; Khairallah, P. A.; Bumpus, F. M. J. Med. Chem. 1979, 22, 1128. (e) Mierke, D. F.; Nössner, G.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 35, 35. (f) Yamazaki, T.; Probstl, A.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 37, 364. (g) Huang, Z.; Probstl, A.; Spencer, J. R.; Yamazaki, T.; Goodman, M. Int. J. Pept. Protein Res. 1993, 42, 352.
26. For some examples documenting these aspects, see: (a) Griffith, O. W. Annu. Rev. Biochem. 1986, 55, 855. (b) Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyawa, H.; Kiso, Y. J. Chem. Soc.; Chem. Commun. 1989, 1678. (c) Rodríguez, M.; Fulcrand, P.; Laur, J.; Aumelas, A.; Ball, J. P.; Martínez, J. J. Med. Chem. 1989, 32, 522. (d) Stachowiak, K.; Khosla, M. C.; Plucinska, K.; Khairallah, P. A.; Bumpus, F. M. J. Med. Chem. 1979, 22, 1128. (e) Mierke, D. F.; Nössner, G.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 35, 35. (f) Yamazaki, T.; Probstl, A.; Schiller, P. W.; Goodman, M. Int. J. Pept. Protein Res. 1991, 37, 364. (g) Huang, Z.; Probstl, A.; Spencer, J. R.; Yamazaki, T.; Goodman, M. Int. J. Pept. Protein Res. 1993, 42, 352.
27. For detailed information on this topic, see: (a) Fernández-Santin, J. M.; Muñoz-Guerra, S.; Rodríguez-Galán, A.; Aymami, J.; Lloveras, J.; Subirana, J. A.; Giralt, E.; Ptak, M. Macromolecules 1987, 20, 62. (b) Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (c) Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. (d) Hintermann, T.; Seebach, D. Synlett 1997, 437. (e) Daura, X.; van Gunsteren, W. F.; Rigo, D.; Jann, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410.
28. For detailed information on this topic, see: (a) Fernández-Santin, J. M.; Muñoz-Guerra, S.; Rodríguez-Galán, A.; Aymami, J.; Lloveras, J.; Subirana, J. A.; Giralt, E.; Ptak, M. Macromolecules 1987, 20, 62. (b) Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (c) Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. (d) Hintermann, T.; Seebach, D. Synlett 1997, 437. (e) Daura, X.; van Gunsteren, W. F.; Rigo, D.; Jann, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410.
29. For detailed information on this topic, see: (a) Fernández-Santin, J. M.; Muñoz-Guerra, S.; Rodríguez-Galán, A.; Aymami, J.; Lloveras, J.; Subirana, J. A.; Giralt, E.; Ptak, M. Macromolecules 1987, 20, 62. (b) Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (c) Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. (d) Hintermann, T.; Seebach, D. Synlett 1997, 437. (e) Daura, X.; van Gunsteren, W. F.; Rigo, D.; Jann, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410.
30. For detailed information on this topic, see: (a) Fernández-Santin, J. M.; Muñoz-Guerra, S.; Rodríguez-Galán, A.; Aymami, J.; Lloveras, J.; Subirana, J. A.; Giralt, E.; Ptak, M. Macromolecules 1987, 20, 62. (b) Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (c) Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. (d) Hintermann, T.; Seebach, D. Synlett 1997, 437. (e) Daura, X.; van Gunsteren, W. F.; Rigo, D.; Jann, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410.
31. For detailed information on this topic, see: (a) Fernández-Santin, J. M.; Muñoz-Guerra, S.; Rodríguez-Galán, A.; Aymami, J.; Lloveras, J.; Subirana, J. A.; Giralt, E.; Ptak, M. Macromolecules 1987, 20, 62. (b) Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. (c) Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. d) Hintermann, T.; Seebach, D. Synlett 1997, 437. (e) Daura, X.; van Gunsteren, W. F.; Rigo, D.; Jann, B.; Seebach, D. Chem. Eur. J. 1997, 3, 1410.
32. For a review on amino acids of the cyclobutane series, see: Avotins, F. Russ. Chem. Rev. 1993, 62, 897.
33. For recent reviews on this topic, see: (a) Cole, D. C. Tetrahedron 1994, 50, 9517. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cardillo, G.; Tomassini, C. Chem. Soc. Rev. 1996, 117. (d) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed., Wiley VCH: New York, 1997.
34. For recent reviews on this topic, see: (a) Cole, D. C. Tetrahedron 1994, 50, 9517. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cardillo, G.; Tomassini, C. Chem. Soc. Rev. 1996, 117. (d) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed., Wiley VCH: New York, 1997.
35. For recent reviews on this topic, see: (a) Cole, D. C. Tetrahedron 1994, 50, 9517. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cardillo, G.; Tomassini, C. Chem. Soc. Rev. 1996, 117. (d) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed., Wiley VCH: New York, 1997.
36. For recent reviews on this topic, see: (a) Cole, D. C. Tetrahedron 1994, 50, 9517. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994, 27, 3. (c) Cardillo, G.; Tomassini, C. Chem. Soc. Rev. 1996, 117. (d) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed., Wiley VCH: New York, 1997.
37. For another approach to β-amino acids enabling direct coupling with α-amino acids, see: Podlech, J.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 471. Also, see: ref 7b.
38. (a) Palomo, C.; Aizpurua, J. M.; Cuevas, C. J. Chem. Soc.; Chem. Commun. 1994, 1957.
39. (b) Palomo, C.; Aizpurua, J. M.; Galarza, R.; Mielgo, A. J. Chem. Soc.; Chem. Commun. 1996, 633. Ibid. Idem. 1996, 1400.
40. (b) Palomo, C.; Aizpurua, J. M.; Galarza, R.; Mielgo, A. J. Chem. Soc.; Chem. Commun. 1996, 633. Ibid. Idem. 1996, 1400.
41. Qjima, I.; Sun, C. M.; Park, Y. H. J. Org. Chem. 1994, 59, 1249.
42. Drey, C. N. C.; Lowbridge, J.; Ridge, R. J. J. Chem. Soc.; Perkin Trans. 1 1973, 2001.
43. For reviews on sulfonyl isocyanates, see: (a) Rasmussen, J. K.; Hassner, A. Chem. Rev. 1976, 76, 389. (b) Dhar, D. N.; Murthy, K. S. K. Synthesis 1986, 437. (c) Kamai, A.; Sattur, P. B. Heterocycles 1987, 26, 1051. For a general review on β-lactams, see: (d) Backes, J. In Houben-Weyl, Methoden der Organischem Chemie; Muller, E., Baeyer, O., Eds; Thieme: Stuttgart, 1991; BandE16B, p 31.
44. For reviews on sulfonyl isocyanates, see: (a) Rasmussen, J. K.; Hassner, A. Chem. Rev. 1976, 76, 389. (b) Dhar, D. N.; Murthy, K. S. K. Synthesis 1986, 437. (c) Kamai, A.; Sattur, P. B. Heterocycles 1987, 26, 1051. For a general review on β-lactams, see: (d) Backes, J. In Houben-Weyl, Methoden der Organischem Chemie; Muller, E., Baeyer, O., Eds; Thieme: Stuttgart, 1991; BandE16B, p 31.
45. For reviews on sulfonyl isocyanates, see: (a) Rasmussen, J. K.; Hassner, A. Chem. Rev. 1976, 76, 389. (b) Dhar, D. N.; Murthy, K. S. K. Synthesis 1986, 437. (c) Kamai, A.; Sattur, P. B. Heterocycles 1987, 26, 1051. For a general review on β-lactams, see: (d) Backes, J. In Houben-Weyl, Methoden der Organischem Chemie; Muller, E., Baeyer, O., Eds; Thieme: Stuttgart, 1991; BandE16B, p 31.
46. For reviews on sulfonyl isocyanates, see: (a) Rasmussen, J. K.; Hassner, A. Chem. Rev. 1976, 76, 389. (b) Dhar, D. N.; Murthy, K. S. K. Synthesis 1986, 437. (c) Kamai, A.; Sattur, P. B. Heterocycles 1987, 26, 1051. For a general review on β-lactams, see: (d) Backes, J. In Houben-Weyl, Methoden der Organischem Chemie; Muller, E., Baeyer, O., Eds; Thieme: Stuttgart, 1991; BandE16B, p 31.
47. Bhupathy, M.; Bergan, J. J.; McNamara, J. M.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 9445.
48. For the use of NaCN to promote ring opening of β-lactams, see: (a) Cavagna, F.; Linkies, H.; Pietsch, H.; Reuschling, D. Angew. Chem., Int. Ed. Engl. 1980, 19, 129. (b) Bose, A. K.; Krishman, L.; Wagle, D. R.; Manhas, M. S. Tetrahedron Lett. 1986, 27, 595. (c) Wagle, D. R.; Monteleone, M. G.; Krishman, L.; Manhas, M. S.; Bose, A. K. J. Chem. Soc.; Chem. Commun. 1989, 8915.
49. For the use of NaCN to promote ring opening of β-lactams, see: (a) Cavagna, F.; Linkies, H.; Pietsch, H.; Reuschling, D. Angew. Chem., Int. Ed. Engl. 1980, 19, 129. (b) Bose, A. K.; Krishman, L.; Wagle, D. R.; Manhas, M. S. Tetrahedron Lett. 1986, 27, 595. (c) Wagle, D. R.; Monteleone, M. G.; Krishman, L.; Manhas, M. S.; Bose, A. K. J. Chem. Soc.; Chem. Commun. 1989, 8915.
50. For the use of NaCN to promote ring opening of β-lactams, see: (a) Cavagna, F.; Linkies, H.; Pietsch, H.; Reuschling, D. Angew. Chem., Int. Ed. Engl. 1980, 19, 129. (b) Bose, A. K.; Krishman, L.; Wagle, D. R.; Manhas, M. S. Tetrahedron Lett. 1986, 27, 595. (c) Wagle, D. R.; Monteleone, M. G.; Krishman, L.; Manhas, M. S.; Bose, A. K. J. Chem. Soc.; Chem. Commun. 1989, 8915.
51. (a) Ave, D. H.; Iwahashi, H.; Shellhamer, D. F. Tetrahedron Lett. 1973, 3719.
52. (b) Durst, T.; O'Sullivan, M. J. J. Org. Chem. 1970, 35, 2043.
53. (c) Barrett, A. G. M.; Betts, M. J.; Fenwick, A. J. Org. Chem. 1985, 50, 169.
54. During preparation of compound 3 an impurity (10-20%) was detected in the reaction. This impurity could be separated from 3 only after forming the Boc-derivative. From the spectroscopic data we assigned structure 3′, which would likely have arised from an acid-catalyzed isomerization of the terminal olefin to the endocyclic olefin, to this impurity. Equation presented.
55. Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Schofield, C. J. Tetrahedron 1990, 46, 4733.
56. Potassium cyanide has also been employed as a catalyst in transesterification processes to remove peptides from the Merrifield resin without racemization of the C-terminal amino acid. For more detailed information, see: Moore, G.; McMaster, D. Int. J. Pept. Protein Res. 1978, 11, 140.
57. (a) Carpino, L. A.; Sadat-Aalaee, D.; Chao, H. G.; DeSelms, R. H. J. Am. Chem. Soc. 1990, 112, 9651.
58. Also, see: (b) Bertho, J.-N.; Loffet, A.; Pinel, C.; Reuther, F.; Sennyey, G. Tetrahedron Lett. 1991, 32, 1303.
59. Kühlein, K.; Jensen, H. Liebigs Ann. Chem. 1974, 369.
60. For detailed information on the factors determining the chemical reactivity of β-lactams, see: The Chemistry of β-Lactams, Page, M. I., Ed.; Chapman and Hall: London, 1992.
61. For pertinent information on methods to couple hindered α-amino acids, see: (a) Spencer, J. R.; Antonenko, U. V.; Delaet, N. G. J.; Goodman, M. Int. J. Pept. Protein 1992, 40, 282. (b) Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397. (c) Angell, Y. M.; García-Eehevarría, C.; Rich, D. H. Tetrahedron Lett. 1994, 35, 5981. (d) Wenschuch, H.; Beyermann, M.; Winter, R.; Bienert, M.; Ionescu, D.; Carpino, L. A. Tetrahedron Lett. 1996, 37, 5483.
62. For pertinent information on methods to couple hindered α-amino acids, see: (a) Spencer, J. R.; Antonenko, U. V.; Delaet, N. G. J.; Goodman, M. Int. J. Pept. Protein 1992, 40, 282. (b) Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397. (c) Angell, Y. M.; García-Eehevarría, C.; Rich, D. H. Tetrahedron Lett. 1994, 35, 5981. (d) Wenschuch, H.; Beyermann, M.; Winter, R.; Bienert, M.; Ionescu, D.; Carpino, L. A. Tetrahedron Lett. 1996, 37, 5483.
63. For pertinent information on methods to couple hindered α-amino acids, see: (a) Spencer, J. R.; Antonenko, U. V.; Delaet, N. G. J.; Goodman, M. Int. J. Pept. Protein 1992, 40, 282. (b) Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397. (c) Angell, Y. M.; García-Eehevarría, C.; Rich, D. H. Tetrahedron Lett. 1994, 35, 5981. (d) Wenschuch, H.; Beyermann, M.; Winter, R.; Bienert, M.; Ionescu, D.; Carpino, L. A. Tetrahedron Lett. 1996, 37, 5483.
64. For pertinent information on methods to couple hindered α-amino acids, see: (a) Spencer, J. R.; Antonenko, U. V.; Delaet, N. G. J.; Goodman, M. Int. J. Pept. Protein 1992, 40, 282. (b) Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397. (c) Angell, Y. M.; García-Eehevarría, C.; Rich, D. H. Tetrahedron Lett. 1994, 35, 5981. (d) Wenschuch, H.; Beyermann, M.; Winter, R.; Bienert, M.; Ionescu, D.; Carpino, L. A. Tetrahedron Lett. 1996, 37, 5483.
65. Chiral HPLC analyses were performed using a 25 cm phase Chiralcel OD analytical column, with a 0.5 mL/min flow of a mixture of ethyl acetate and hexane. In all cases the R enantiomer showed a shorter retention time.
66. For a recent review on β-amino acids and their derivatives from β-lactams, see: Palomo, C.; Aizpurua, J. M.; Ganboa, I., in ref 9d, p 279.