Rapid entry to enantiopure polycyclic β-lactams via intramolecular nitrone-alkene cycloaddition of 2-azetidinone-tethered alkenylaldehydes

Tetrahedron Letters

Volumn 40, Issue 29, 1999, Pages 5391-5394

  Alcaide, Benito ^a   Alonso, Jose M ^a   Aly, Moustafa F ^a   Sáez, Elena ^a   Martínez Alcázar, M Paz ^b   Hernández Cano, Félix ^c  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD SAN PABLO CEU   (Spain)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; ALDEHYDE; BETA LACTAM;

ARTICLE; ENANTIOMER; MOLECULAR INTERACTION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0033575466     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01013-8     Document Type: Article

References (41)

1. Permanent address: Department of Chemistry, Faculty of Science at Qena, South Valley University, Qena, Egypt.
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3. For a brief account of his work, see: Lebel, N. A. Trans. N. Y. Acad. Sci. 1965, 27, 858.
4. For reviews on nitrone cycloaddition reaction in organic synthesis, see: a) Tufariello, J.J. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A. Ed.; John Wiley and Sons; New York, 1984, Vol. 2; Chapter 9; p. 83-168. b) Wade, P. A. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I; Semmelhack, M. E. Eds.; Pergamon Press, Oxford 1991, Vol. 4, Ch. 4.10, pp. 1111-1168. c) Frederickson, M. Tetrahedron 1997, 53, 403. d) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
5. For reviews on nitrone cycloaddition reaction in organic synthesis, see: a) Tufariello, J.J. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A. Ed.; John Wiley and Sons; New York, 1984, Vol. 2; Chapter 9; p. 83-168. b) Wade, P. A. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I; Semmelhack, M. E. Eds.; Pergamon Press, Oxford 1991, Vol. 4, Ch. 4.10, pp. 1111-1168. c) Frederickson, M. Tetrahedron 1997, 53, 403. d) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
6. For reviews on nitrone cycloaddition reaction in organic synthesis, see: a) Tufariello, J.J. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A. Ed.; John Wiley and Sons; New York, 1984, Vol. 2; Chapter 9; p. 83-168. b) Wade, P. A. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I; Semmelhack, M. E. Eds.; Pergamon Press, Oxford 1991, Vol. 4, Ch. 4.10, pp. 1111-1168. c) Frederickson, M. Tetrahedron 1997, 53, 403. d) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
7. For reviews on nitrone cycloaddition reaction in organic synthesis, see: a) Tufariello, J.J. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A. Ed.; John Wiley and Sons; New York, 1984, Vol. 2; Chapter 9; p. 83-168. b) Wade, P. A. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I; Semmelhack, M. E. Eds.; Pergamon Press, Oxford 1991, Vol. 4, Ch. 4.10, pp. 1111-1168. c) Frederickson, M. Tetrahedron 1997, 53, 403. d) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
8. a) Alcaide, B.; Rodríguez-Vicente, A Tetrahedron Lett. 1998, 39, 6589. b) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. c) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901. d) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125 e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M.A. Tetrahedron: Asymmetry 1996, 7, 2203.
9. a) Alcaide, B.; Rodríguez-Vicente, A Tetrahedron Lett. 1998, 39, 6589. b) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. c) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901. d) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125 e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M.A. Tetrahedron: Asymmetry 1996, 7, 2203.
10. a) Alcaide, B.; Rodríguez-Vicente, A Tetrahedron Lett. 1998, 39, 6589. b) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. c) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901. d) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125 e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M.A. Tetrahedron: Asymmetry 1996, 7, 2203.
11. a) Alcaide, B.; Rodríguez-Vicente, A Tetrahedron Lett. 1998, 39, 6589. b) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. c) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901. d) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125 e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M.A. Tetrahedron: Asymmetry 1996, 7, 2203.
12. a) Alcaide, B.; Rodríguez-Vicente, A Tetrahedron Lett. 1998, 39, 6589. b) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. c) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901. d) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125 e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M.A. Tetrahedron: Asymmetry 1996, 7, 2203.
13. Alcaide, B.; Almendros, P. Tetrahedron Lett. 1999, 40, 1015.
14. INAC reactions of aliphatic 2-substituted 5-hexenyl and 5-heptenyl nitrones have been successfully used for the synthesis of key monocyclic intermediates of 1β-methylthienamycin. A notable feature of such processes is their propensity for the predominant formation of the fused bicyclic systems as opposed to the bridged systems. See, for example: a) Kang, S. H.; Kim, W. J. Synlett. 1991, 520. b) Kang, S. H.; Lee, H. S. Tetrahedron Lett. 1995, 36, 6713. b) Junk, M. E.;Vu, B. T. J. Org. Chem. 1996, 61, 4427.
15. INAC reactions of aliphatic 2-substituted 5-hexenyl and 5-heptenyl nitrones have been successfully used for the synthesis of key monocyclic intermediates of 1β-methylthienamycin. A notable feature of such processes is their propensity for the predominant formation of the fused bicyclic systems as opposed to the bridged systems. See, for example: a) Kang, S. H.; Kim, W. J. Synlett. 1991, 520. b) Kang, S. H.; Lee, H. S. Tetrahedron Lett. 1995, 36, 6713. b) Junk, M. E.;Vu, B. T. J. Org. Chem. 1996, 61, 4427.
16. INAC reactions of aliphatic 2-substituted 5-hexenyl and 5-heptenyl nitrones have been successfully used for the synthesis of key monocyclic intermediates of 1β-methylthienamycin. A notable feature of such processes is their propensity for the predominant formation of the fused bicyclic systems as opposed to the bridged systems. See, for example: a) Kang, S. H.; Kim, W. J. Synlett. 1991, 520. b) Kang, S. H.; Lee, H. S. Tetrahedron Lett. 1995, 36, 6713. b) Junk, M. E.;Vu, B. T. J. Org. Chem. 1996, 61, 4427.
17. For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
18. For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
19. For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
20. For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
21. For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
22. See, for instance: a) van Boggelen, M. P.; van Dommelen, B. F. G. A.; Jiang, Sh.; Singh, G. Tetrahedron 1997, 53, 16897. b) Tsay, S.-C.; Patel, H. V.; Hwu, J. R. Synlett. 1998, 939.
23. See, for instance: a) van Boggelen, M. P.; van Dommelen, B. F. G. A.; Jiang, Sh.; Singh, G. Tetrahedron 1997, 53, 16897. b) Tsay, S.-C.; Patel, H. V.; Hwu, J. R. Synlett. 1998, 939.
24. a) (g) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227. b) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Ch. 3, p 295.
25. a) (g) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227. b) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Ch. 3, p 295.
26. -1; F(000) = 552. A colourless crystal of 0.66×0.16×0.16 mm was used. 1210 independent reflections were collected on four circle Seifert XRD 3000S difractometer. The structure was solved by direct methods (SIR92 and difference Fourier techniques; not absorption correction was applied (m = 0.79 mm-1); all calculations were done with the program SHELX97 on a VAX 6410 computer. The structure was refined using full matrix least-squares procedures. Coordinates have been deposited at the Cambridge Crystallographic Data Centre. Figure. Crystal structure of (-)-3a (equation presented)
27. Chiacchio, U.; Casuscelli, F.; Corsaro, A.; Librando, V.; Rescifina, A.; Romeo, R.; Romeo, G. Tetrahedron 1995, 51, 5689. For related oxime-olefin (IOOC) reactions, see: Falb, E.; Bechor, Y.; Nudelman, A.; Hassner, A.; Albeck, A.;Gottlieb, H. E. J. Org. Chem. 1999, 64, 498.
28. Chiacchio, U.; Casuscelli, F.; Corsaro, A.; Librando, V.; Rescifina, A.; Romeo, R.; Romeo, G. Tetrahedron 1995, 51, 5689. For related oxime-olefin (IOOC) reactions, see: Falb, E.; Bechor, Y.; Nudelman, A.; Hassner, A.; Albeck, A.;Gottlieb, H. E. J. Org. Chem. 1999, 64, 498.
29. a) Alcaide, B.; Martín-Cantalejo, Y.; Plumet, J.; Rodriguez-López, J.; Sierra, M. A. Tetrahedron Lett., 1991, 32, 803. b) Alcaide, B.; Martín-Cantalejo, Y.; Pérez-Castells, J.; Rodríguez-López, J.; Sierra, M.A; Monge, A.; Pérez-García, V. J. Org. Chem., 1992, 57, 5921.
30. a) Alcaide, B.; Martín-Cantalejo, Y.; Plumet, J.; Rodriguez-López, J.; Sierra, M. A. Tetrahedron Lett., 1991, 32, 803. b) Alcaide, B.; Martín-Cantalejo, Y.; Pérez-Castells, J.; Rodríguez-López, J.; Sierra, M.A; Monge, A.; Pérez-García, V. J. Org. Chem., 1992, 57, 5921.
31. See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
32. See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
33. See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
34. See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
35. See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
36. See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
37. See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
38. The salient features which distinguished between the two regioisomers (2a and 3a, for example) was the presence, in the NMR spectrum of compound 2a, of a highfield one proton multiplet at δ(H) 2.78 coupled to five other protons and a methine carbon signal at δ(C) 37.8 (DEPT), which would be expected for the C-8 methine in the fused structure 2a. Also, this compound showed two methylene carbon resonances at δ(C) 60.8 and 68.6 (DEPT) attributable to two oxygen substituted methylene carbons. Compound 3a displayed a highfield geminally coupled (12.7 Hz) proton signals at δ(H) 2.40 (m) and 1.92 (d), and a methylene carbon resonance at δ(C)28.5 (DEPT), and was consistent with its bridged structure.
39. Walts, A. E.; Roush, W. R. Tetrahedron 1985, 41, 3463.
40. Swern, D.; Omura, K. Tetrahedron 1978, 34, 1651.
41. All new compounds gave satisfactory analytical and spectral data.