Stereoselective synthesis of 3-substituted 4-(formyloxy)-2-azetidinones by the unusual Baeyer-Villiger reaction of β-lactam aldehydes. Scope and synthetic applications

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8819-8825

  Alcaide, Benito ^a,b   Alyt, Moustafa F ^a   Sierra, Miguel A ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b SOUTH VALLEY UNIVERSITY   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030458583     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9612685     Document Type: Article

References (66)

1. For a preliminary communication of part of this work see: Alcaide, B.; Aly, M. F.; Sierra, M. A. Tetrahedron Lett. 1995,36,3401-4.
2. For recent reviews of Baeyer-Villiger reaction, see: (a) Krow, G. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 7, p 671.
3. (b) Krow, G. R. Organic Reactions; Paquette, L. A., Ed.; John Willey and Sons: New York, 1993; Vol. 43, p 251.
4. Krow, G. R. Tetrahedron 1981,37, 2697.
5. For récent papers, see: (a) Kaneda, K.; Ueno, S.; Imanaka, T.; Shimotsuma, E.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1994, 59, 2915.
6. (b) Chida, N.; Tobe, T.; Ogawa, S. Tetrahedron Lett. 1994, 35, 7249.
7. See, for example: (a) Grosby, D. G. J. Org. Chem. 1961,26,1215.
8. (b) Ogata, Y.; Sawaki, Y. J. Org. Chem. 1969,34, 3985.
9. Godfrey, I. M.; Sargent, M. V.; Elix, J. A. J. Chem. Soc., Perkin Trans, 1 1974, 1353.
10. Camps, F.; Coll, J.; Messeguer, A.; Pericds, M. A. Tetrahedron Lett. 1981, 22, 3895.
11. (e) Gammill, R. B.; Hyde, B. R. J. Org. Chem. 1983, 48, 3863.
12. (f) Nelson, W. L.; Burke, T. R. J. Med. Chem. 1979, 22, 1082.
13. See, for example: (a) Masman, J.-A. H.; Pensar, K. G. Synthesis 1985, 786.
14. (b) Langendoen, A.; Koomen, G.-J.; Pandit, U. K. Heterocycles 1987, 26, 91.
15. Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1989, 1237.
16. DeBoer, A.; Ellwanger, R. E. J. Org. Chem. 1974, 39, 77.
17. See, for example: (a) Ojima, I. Adv. Asymm. Synth. 1995,1, 95.
18. (b) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988,27,1755.
19. Alcaide, B.; Miranda, M.; Pérez-Castells, J.; Sierra, M. A. J. Org. Chem. 1993, 58, 297.
20. Alcaide, B.; Martin-Cantalejo, Y.; Rodriguez-Löpez, J.; Sierra, M. A. J. Org. Chem. 1993, 58, 4767.
21. (e) Alcaide, B.; Pérez-Castells, J.; Polanco, C.; Sierra, M. A. J. Org. Chem., 1995, 60, 6012.
22. For comprehensive reviews, see: (a) Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982,17, 463.
23. (b) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729.
24. Davies, D. E.; Storr, R. C. In Comprehensive Heterocydic Chemistry; Lwowski, W., Ed.; Pergamon: New York, 1984; Vol. 7, p 237.
25. Wild, H. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers, Inc.: New York, 1993; Chapter 2, p 49.
26. Gavina, F.; Costero, A. M.; Andreu, M. R. J. Org. Chem. 1990, 55, 434 and references cited therein.
27. Klaus, K.; Grimm, D.; Prossel, G. LiebigsAnn. Chem. 1974,539.
28. For reviews on CSI, see: (a) Rasmussen, J. K.; Hassner, A. Chem. Rev. 1976, 76, 389.
29. (b) Dhar, D. N.; Murthy, K. S. K. Synthesis 1986, 437.
30. Kamai, A.; Sattur, P. B. Heterocydes 1987, 26, 1051.
31. See, for example: (a) Murahashi, S.-I; Naota, T.; Kawabara, T.; Saito, T.; Kumobayashi, H.; Akutawa, S. J. Am. Chem. Soc. 1990, 112,7820.
32. (b) Easton, C. J.; Love, S. G.; Wang, P. J. Chem. Soc., Perkin Trans. 1 1990, 277.
33. Mori, M.; Kagechica, K.; Tohjima, K.; Shibasaki, M. Tetrahedron Lett. 1988, 29, 1409.
34. (a) Kehagia, K.; Ugi, I. Tetrahedron 1995,51, 9523.
35. (b) Georg, G. L; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 709, 1129.
36. Cainelli, G.; Contento, M.; Giacomini, D.; Panunzio, M. Tetrahedron Lett. 1985, 26, 937.
37. (a) Tschaen, D. M.; Fuentes, L. M.; Lynch, J. E.; Laswell, W. L.; Volante, R. P.; Shinkari, I. Tetrahedron Lett. 1988, 29, 2779.
38. (b) Altamura, M.; Ricci, M. Synth. Commun. 1988,18, 2129.
39. (a) Sheppard, A.; Miller, M. J. J. Chem. Soc., Perkin Trans, 1 1990, 2519.
40. (b) Palomo, C.; Cossio, F. P.; Arrieta, A.; Odriozola, J. M.; Oiarbide, M.; Ontoria, J. M. C. J. Org. Chem. 1989, 54, 5736.
41. Arrieta, A.; Lecea, B.; Cossio, F. P.; Palomo, C. J. Org. Chem. 1988, 53, 3784.
42. (a) Alcaide, B.; Martîn-Cantalejo, Y.; Plumet, J.; Rodriguez-Löpez, J.; Sierra, M. A. Tetrahedron Lett. 1991, 32, 803.
43. (b) Alcaide, B.; Marti'n-Cantalejo, Y.; Pérez-Castells, J.; Rodriguez-Löpez, J.; Sierra, M. A.; Monge, A.; Perez-Garcfa, V. J. Org. Chem. 1992, 57, 5921.
44. (a) Alcaide, B.; Gömez, A.; Plumet, J.; Rodrfguez-Löpez, J. Tetrahedron 1989, 45, 2751.
45. (b) Alcaide, B.; Esteban, G.; MartfnCantalejo, Y.; Plumet, J.; Rodriguez-Löpez, J.; Monge, A.; Perez-Garcfa, V. J. Org. Chem. 1994, 59, 7994.
46. Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985,26, 3783.
47. For other enantidspecific syntheses of cis-4-formyl-2-azetidinones see, for example: (a) Jarayaman, M.; Deshmukh, A. R.- A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 5921.
48. (b) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; MartînezRipoll, M. J. Am. Chem. Soc. 1992, 114, 9360.
49. Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065.
50. The stereochemical outcome of β-lactams derived from D-glyceraldehyde acetonide has been determined both experimentally and theoretically. For the experimental approach see: (a) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983,66, 2206.
51. (b) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454.
52. Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Böse, A. K. J. Org. Chem. 1988, 53, 4227
53. and references therein. For the theoretical approach see, for example: Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085.
54. The sole exception was the 3-(phenylthio)-4-formyl-2-azetidinone. This compound gave the corresponding sulfone after prolongued reaction time. In this case the formyl group remained unaltered.
55. Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
56. 4 reduction on-related 4-acetoxy β-lactams, see: Pfaendler, H. R.; Hoppe, H. Heterocydes 1985, 23, 265.
57. For another reduction method, see: Arrieta, A.; Lecea, B.; Cossio, F. P.; Palomo, C. J. Org. Chem. 1988, 53, 3784.
58. Abouabdellah, A.; Welch, J. T. Tetrahedron: Asymmetry 1994, 5, 1005.
59. (a) Aoki, H.; Sakai, H.; Kohsaka, M.; Konomi, T.; Hosoda, J.; Kubochi, Y.; Iguchi, E.; Imanaka, H. J. Anlibiot. 1976,29, 492, 890.
60. (b) Hashimoto, M.; Komori, T.; Kamiya, T. J. Am. Chem. Soc. 1976, 98, 3023.
61. Hosoda, J.; Konomi, T.; Tani, N.; Aoki, H.; Imanaka, H. Agric. Biol. Chem. 1977, 41, 2013.
62. (a) Iraada, A.; Kitano, K.; Kintaka, K.; Muroi, M.; Asai, M. Nature (London) 1981, 289, 590.
63. (b) Sykes, R. B.; Cimarusti, C. M.; Bonner, D. P.; Bush, K.; Floyd, D. M.; Georgopapadakou, N. H.; Koster, W. H.; Liu, W. C.; Parker, W. L.; Principe, P. A.; Rathnum, M. L.; Slusarchyk, W. A.; Trejo, W. H.; Wells, J. S. Nature (London) 1981, 291, 489.
64. Wells, J. S.; Hunter, J. C.; Astle, G. L.; Sherwood, J. C.; Ricca, C. M.; Trejo, W. H.; Bonner, D. P.; Sykes, R. B. J. Antibiot. 1982, 35, 814.
65. Stuart, W. W. Nature (London) 1971, 229, 174.
66. Full spectroscopic and analytical data of compounds not included in this Experimental Section are described in the Supporting Information.