Synthesis of enantiopure 1,2-didehydropyrrolidine, D-proline, and oxazoline derivatives via Staudinger-aza-Wittig cyclization of γ-azido aldehydes

Synthesis

Volumn , Issue 1, 1996, Pages 123-132

  Mulzer, Johann ^a   Meier, Andreas ^a   Buschmann, Jürgen ^b   Luger, Peter ^b  

^a GOETHE UNIVERSITY   (Germany)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

cyanosilylation; cyclic imines; oxazoline; peptidomimetics; Staudinger cyclization

Indexed keywords

OXAZOLINE DERIVATIVE; PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030045893     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4162     Document Type: Article

References (36)

1. (a) Hirschmann, R. Angew. Chem. 1991, 103, 1305; Angew. Chem. Int. Ed. Engl. 1991, 30, 1278.
2. (a) Hirschmann, R. Angew. Chem. 1991, 103, 1305; Angew. Chem. Int. Ed. Engl. 1991, 30, 1278.
3. (b) Hölzemann, G. Kontakte (Darmstadt) 1991 (1), 3.
4. (c) A. Giannis, A.; Kolter, T. Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244.
5. (c) A. Giannis, A.; Kolter, T. Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244.
6. Degrado, W. F. Adv. Protein Chem. 1988, 39, 51.
7. (a) Stein, R. L. Adv. Protein Chem. 1993, 44, 1.
8. (b) G. Fischer, Angew. Chem. 1994, 106, 1479; Angew. Chem. Int. Ed. Engl. 1994, 33, 1415.
9. (b) G. Fischer, Angew. Chem. 1994, 106, 1479; Angew. Chem. Int. Ed. Engl. 1994, 33, 1415.
10. (a) Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1.
11. (b) Barlow, D. J.; Thornton, J. M. J. Mol. Biol. 1988, 201, 601.
12. (a) Hruby, V. J. Trends in Pharmacol. Sci. 1985, 6, 259.
13. (b) Hruby, V. J. Trends in Pharmacol. Sci. 1987, 8, 336.
14. (c) Purisiama, E.; Scheraga, H. J. Mol. Biol. 1987, 196, 697.
15. (a) Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270.
16. (b) Rapoport, H.; Koskinen, A. M. P. J. Org. Chem. 1989, 54, 1859.
17. (c) Björgling, F.; Boutelje, J.; Hijalmarsson, M.; Hult, K.; Norin, T. J. Chem. Soc., Chem. Commun. 1987, 1041.
18. (d) Mauger, A. B.; Wittkop, B. Chem. Rev. 1966, 66, 47.
19. (e) Ohta, T.; Hosoi, A.; Kimura, T.; Nozoe, S. Chem. Lett. 1987, 2091, 2229.
20. (a) Mulzer, J.; Kappert, M. Angew. Chem. 1983, 95, 60; Angew. Chem. Int. Ed. Engl. 1983, 22, 63.
21. (a) Mulzer, J.; Kappert, M. Angew. Chem. 1983, 95, 60; Angew. Chem. Int. Ed. Engl. 1983, 22, 63.
22. (b) Mulzer, J.; Kappert, M. Tetrahedron Lett. 1985, 26, 1631.
23. (c) Schmid, C. R.; Bryant, J. D.; Dowlatzedah, M.; Phillips, J. L.; Prather, D. E.; Schantz, R. D.; Sear, N. L.; Vianco, C. S. J. Org. Chem. 1991, 56, 4056.
24. (d) Mulzer, J.; Meier, A. unpublished results.
25. (e) For enantiomeric compounds to 2 and 2b see: Mulzer, J.; Graske, K.-D.; Kirste, B. Liebigs Ann. Chem. 1988, 891.
26. Staudinger-aza-Wittig cyclizations have been reported for azido ketones: (a) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Chem. Soc., Chem. Comm. 1982, 1224. (b) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352. (c) Lambert, P. H.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1986, 83. Reviews on Staudinger-aza-Wittig cyclizations: (a) Eguchi, E.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) Eguchi, E.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. 1992, 24, 209. (c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197. (d) Saunders, S. A.; Foster, S. A.; Leyston, L. J. J. Chem. Soc., Chem. Comm. 1973, 29. (e) Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 727, 231. (f) Lee, K.-J. Synthesis 1984, 455.
27. Staudinger-aza-Wittig cyclizations have been reported for azido ketones: (a) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Chem. Soc., Chem. Comm. 1982, 1224. (b) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352. (c) Lambert, P. H.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1986, 83. Reviews on Staudinger-aza-Wittig cyclizations: (a) Eguchi, E.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) Eguchi, E.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. 1992, 24, 209. (c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197. (d) Saunders, S. A.; Foster, S. A.; Leyston, L. J. J. Chem. Soc., Chem. Comm. 1973, 29. (e) Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 727, 231. (f) Lee, K.-J. Synthesis 1984, 455.
28. Staudinger-aza-Wittig cyclizations have been reported for azido ketones: (a) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Chem. Soc., Chem. Comm. 1982, 1224. (b) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352. (c) Lambert, P. H.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1986, 83. Reviews on Staudinger-aza-Wittig cyclizations: (a) Eguchi, E.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) Eguchi, E.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. 1992, 24, 209. (c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197. (d) Saunders, S. A.; Foster, S. A.; Leyston, L. J. J. Chem. Soc., Chem. Comm. 1973, 29. (e) Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 727, 231. (f) Lee, K.-J. Synthesis 1984, 455.
29. Staudinger-aza-Wittig cyclizations have been reported for azido ketones: (a) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Chem. Soc., Chem. Comm. 1982, 1224. (b) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352. (c) Lambert, P. H.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1986, 83. Reviews on Staudinger-aza-Wittig cyclizations: (a) Eguchi, E.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) Eguchi, E.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. 1992, 24, 209. (c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197. (d) Saunders, S. A.; Foster, S. A.; Leyston, L. J. J. Chem. Soc., Chem. Comm. 1973, 29. (e) Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 727, 231. (f) Lee, K.-J. Synthesis 1984, 455.
30. Staudinger-aza-Wittig cyclizations have been reported for azido ketones: (a) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Chem. Soc., Chem. Comm. 1982, 1224. (b) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352. (c) Lambert, P. H.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1986, 83. Reviews on Staudinger-aza-Wittig cyclizations: (a) Eguchi, E.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) Eguchi, E.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. 1992, 24, 209. (c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197. (d) Saunders, S. A.; Foster, S. A.; Leyston, L. J. J. Chem. Soc., Chem. Comm. 1973, 29. (e) Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 727, 231. (f) Lee, K.-J. Synthesis 1984, 455.
31. Staudinger-aza-Wittig cyclizations have been reported for azido ketones: (a) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Chem. Soc., Chem. Comm. 1982, 1224. (b) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352. (c) Lambert, P. H.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1986, 83. Reviews on Staudinger-aza-Wittig cyclizations: (a) Eguchi, E.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) Eguchi, E.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. 1992, 24, 209. (c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197. (d) Saunders, S. A.; Foster, S. A.; Leyston, L. J. J. Chem. Soc., Chem. Comm. 1973, 29. (e) Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 727, 231. (f) Lee, K.-J. Synthesis 1984, 455.
32. Staudinger-aza-Wittig cyclizations have been reported for azido ketones: (a) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Chem. Soc., Chem. Comm. 1982, 1224. (b) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352. (c) Lambert, P. H.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1986, 83. Reviews on Staudinger-aza-Wittig cyclizations: (a) Eguchi, E.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) Eguchi, E.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. 1992, 24, 209. (c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197. (d) Saunders, S. A.; Foster, S. A.; Leyston, L. J. J. Chem. Soc., Chem. Comm. 1973, 29. (e) Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 727, 231. (f) Lee, K.-J. Synthesis 1984, 455.
33. Staudinger-aza-Wittig cyclizations have been reported for azido ketones: (a) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Chem. Soc., Chem. Comm. 1982, 1224. (b) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352. (c) Lambert, P. H.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1986, 83. Reviews on Staudinger-aza-Wittig cyclizations: (a) Eguchi, E.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) Eguchi, E.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. 1992, 24, 209. (c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197. (d) Saunders, S. A.; Foster, S. A.; Leyston, L. J. J. Chem. Soc., Chem. Comm. 1973, 29. (e) Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 727, 231. (f) Lee, K.-J. Synthesis 1984, 455.
34. Staudinger-aza-Wittig cyclizations have been reported for azido ketones: (a) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Chem. Soc., Chem. Comm. 1982, 1224. (b) Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352. (c) Lambert, P. H.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1986, 83. Reviews on Staudinger-aza-Wittig cyclizations: (a) Eguchi, E.; Yamashita, K.; Matsushita, Y.; Kakehi, A. J. Org. Chem. 1995, 60, 4006. (b) Eguchi, E.; Matsushita, Y.; Yamashita, K. Org. Prep. Proced. 1992, 24, 209. (c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197. (d) Saunders, S. A.; Foster, S. A.; Leyston, L. J. J. Chem. Soc., Chem. Comm. 1973, 29. (e) Zbiral, E.; Stroh, J. Liebigs Ann. Chem. 1969, 727, 231. (f) Lee, K.-J. Synthesis 1984, 455.
35. (a) Ojima, I.; Inaba, S.; Nakatsugawa, K. Chem. Lett. 1975, 331.
36. (b) Ojima, I.; Inaba, S. Chem. Lett. 1975, 737.