Catalytic, asymmetric synthesis of β-lactams [11]

Journal of the American Chemical Society

Volumn 122, Issue 32, 2000, Pages 7831-7832

  Taggi, Andrew E ^a   Hafez, Ahmed M ^a   Wack, Harald ^a   Young, Brandon ^a   Drury III, William J ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; IMINE; KETENE DERIVATIVE;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; LETTER; STEREOCHEMISTRY;

EID: 0034674972     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001754g     Document Type: Letter

References (34)

1. For a general review: De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Padwa, A. Eds.; Pergamon: Oxford, 1996; Vol 1B, p 507.
2. For a general account: Wilmouth, R. C.; Kassamally, S.; Westwood, N. J.; Sheppard, R. J.; Claridge, T. D. W.; Aplin, R. T.; Wright, P. A.; Pritchard, G. J.; Schofield, C. J. Biochemistry 1999, 38, 7989.
3. Review: Palomo, C.; Aizpurua, J. M.; Iñaki, G.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223, 3.
4. (a) Davoli, P.; Moretti, I.; Prati, F.; Alper, H. J. Org. Chem. 1999, 64, 518.
5. (b) Calet, S.; Urso, F.; Alper, H. J. Am. Chem. Soc. 1989, 111, 931.
6. Wack, H.; Drury, W. J., III; Taggi, A. E.; Ferraris, D.; Lectka, T. Org. Lett. 1999, 1, 1985.
7. We have used α-imino ester 2a in the catalytic, asymmetric synthesis of α-amino acid derivatives: (a) Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Imine 2a was first used in work by: Tschaen, D. H.; Turos, E.; Weinreb, S. M. J. Org. Chem. 1984, 49, 5058.
8. We have used α-imino ester 2a in the catalytic, asymmetric synthesis of α-amino acid derivatives: (a) Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Imine 2a was first used in work by: Tschaen, D. H.; Turos, E.; Weinreb, S. M. J. Org. Chem. 1984, 49, 5058.
9. We have used α-imino ester 2a in the catalytic, asymmetric synthesis of α-amino acid derivatives: (a) Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 11006. (b) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548. Imine 2a was first used in work by: Tschaen, D. H.; Turos, E.; Weinreb, S. M. J. Org. Chem. 1984, 49, 5058.
10. Ring opening of β-lactams under mild conditions provides access to various optically pure β-amino acid derivatives whose synthesis is of recent interest, see: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959.
11. Hydrogen bond contacts have been postulated to play similar roles in the Baylis-Hillman reaction: Ameer, F.; Drewes, S. E.; Freese, S.; Kaye, P. T. Synth Commun. 1988, 18, 495.
12. For other, excellent uses of cinchona alkaloids in asymmetric synthesis see: Ester synthesis; (a) Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157. Lactone synthesis; (b) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166. Ketene dimerization; Calter, M. A. J. Org. Chem. 1996, 61, 8006. Calter, M. A.; Guo, X. J. Org. Chem. 1998, 63, 5308. Baylis-Hillman reaction; (e) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatukeyama, S. J. Am. Chem. Soc. 1999, 120, 10219. Osmylation reactions; (f) Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Phase-transfer catalysis; (g) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1999, 120, 13000.
13. For other, excellent uses of cinchona alkaloids in asymmetric synthesis see: Ester synthesis; (a) Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157. Lactone synthesis; (b) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166. Ketene dimerization; Calter, M. A. J. Org. Chem. 1996, 61, 8006. Calter, M. A.; Guo, X. J. Org. Chem. 1998, 63, 5308. Baylis-Hillman reaction; (e) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatukeyama, S. J. Am. Chem. Soc. 1999, 120, 10219. Osmylation reactions; (f) Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Phase-transfer catalysis; (g) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1999, 120, 13000.
14. For other, excellent uses of cinchona alkaloids in asymmetric synthesis see: Ester synthesis; (a) Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157. Lactone synthesis; (b) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166. Ketene dimerization; Calter, M. A. J. Org. Chem. 1996, 61, 8006. Calter, M. A.; Guo, X. J. Org. Chem. 1998, 63, 5308. Baylis-Hillman reaction; (e) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatukeyama, S. J. Am. Chem. Soc. 1999, 120, 10219. Osmylation reactions; (f) Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Phase-transfer catalysis; (g) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1999, 120, 13000.
15. For other, excellent uses of cinchona alkaloids in asymmetric synthesis see: Ester synthesis; (a) Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157. Lactone synthesis; (b) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166. Ketene dimerization; Calter, M. A. J. Org. Chem. 1996, 61, 8006. Calter, M. A.; Guo, X. J. Org. Chem. 1998, 63, 5308. Baylis-Hillman reaction; (e) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatukeyama, S. J. Am. Chem. Soc. 1999, 120, 10219. Osmylation reactions; (f) Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Phase-transfer catalysis; (g) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1999, 120, 13000.
16. For other, excellent uses of cinchona alkaloids in asymmetric synthesis see: Ester synthesis; (a) Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157. Lactone synthesis; (b) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166. Ketene dimerization; Calter, M. A. J. Org. Chem. 1996, 61, 8006. Calter, M. A.; Guo, X. J. Org. Chem. 1998, 63, 5308. Baylis-Hillman reaction; (e) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatukeyama, S. J. Am. Chem. Soc. 1999, 120, 10219. Osmylation reactions; (f) Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Phase-transfer catalysis; (g) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1999, 120, 13000.
17. For other, excellent uses of cinchona alkaloids in asymmetric synthesis see: Ester synthesis; (a) Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157. Lactone synthesis; (b) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166. Ketene dimerization; Calter, M. A. J. Org. Chem. 1996, 61, 8006. Calter, M. A.; Guo, X. J. Org. Chem. 1998, 63, 5308. Baylis-Hillman reaction; (e) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatukeyama, S. J. Am. Chem. Soc. 1999, 120, 10219. Osmylation reactions; (f) Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Phase-transfer catalysis; (g) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1999, 120, 13000.
18. For other, excellent uses of cinchona alkaloids in asymmetric synthesis see: Ester synthesis; (a) Samtleben, R.; Pracejus, H. J. Prakt. Chem. 1972, 314, 157. Lactone synthesis; (b) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166. Ketene dimerization; Calter, M. A. J. Org. Chem. 1996, 61, 8006. Calter, M. A.; Guo, X. J. Org. Chem. 1998, 63, 5308. Baylis-Hillman reaction; (e) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatukeyama, S. J. Am. Chem. Soc. 1999, 120, 10219. Osmylation reactions; (f) Kolb, H. C.; VanNieuwenzhe, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. Phase-transfer catalysis; (g) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1999, 120, 13000.
19. (h) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353. Peptide based catalysis;
20. Jarvo, E. R, Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J. Jr.; Miller, S. J. J. Am. Chem. Soc. 1999; 121; 11638.
21. Pracejus, H.; Maetie, H.; J. Prakt. Chem. 1964, 24, 195.
22. For further details on the conduct of this reaction, including stereochemical proofs, see the Supporting Information.
23. Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742. Additional information can be found in: Tidwell, T. T. Ketenes; John Wiley & Sons: New York, 1995.
24. Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742. Additional information can be found in: Tidwell, T. T. Ketenes; John Wiley & Sons: New York, 1995.
25. A procedure for the in situ generation of ketenes, utilizing basic scavenger resins, is under development and will be published in due course.
26. (a) Hibbert, F.; Emsley, J. Adv. Phys. Org. Chem. 1990, 26, 255.
27. (b) Alder, R. W. Chem. Rev. 1989, 89, 1215.
28. See the Supporting Information for general procedures.
29. The nonoptimal yields may be due to slow polymerization of the imine.
30. β-Lactam 1d has been investigated by DuPont-Merck as an inhibitor of human elastase: Firestone, R. A.; Barker, P. L.; Pisano, J. M.; Ashe, B. M.; Dahlgren, M. E. Tetrahedron 1990, 46, 2255.
31. Ring opening of these β-lactams provides entry to various syn-alkyl-substituted aspartic acids. For a previous synthesis from β, β-disubstituted α-enamides through catalytic hydrogenation, see: (a) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375. Synthesis from β-lactams; (b) Palomo, C.; Aizpurua, J. M.; Ontoria, J. M.; Iturburu, M. Tetrahedron Lett. 1992, 33, 4823.
32. Ring opening of these β-lactams provides entry to various syn-alkyl- substituted aspartic acids. For a previous synthesis from β, β-disubstituted α-enamides through catalytic hydrogenation, see: (a) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375. Synthesis from β-lactams; (b) Palomo, C.; Aizpurua, J. M.; Ontoria, J. M.; Iturburu, M. Tetrahedron Lett. 1992, 33, 4823.
33. In propionitrile solvent, benzoylquinine 6a functions as a highly diastereoeselective catalyst, yielding product 1c with a dr of 95/5.
34. 2 is known to deprotect N-benzyloxy β-lactams: (a) Romo, D.; Rzasa, R. M.; Shea, H. A.; Park, K.; Langenhan, J. M.; Sun, L.; Akhiezer, A.; Liu, J. O. J. Am. Chem. Soc. 1998, 120, 12237.