Yb(OTf)3-catalyzed one-pot synthesis of β-lactams from silyl ketene thioacetals by a two- or a three-component reaction

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8293-8296

  Annunziata, Rita ^a   Cinquini, Mauro ^a   Cozzi, Franco ^a   Molteni, Valentina ^a   Schupp, Olaf ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345230256     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960844u     Document Type: Article

References (56)

1. (a) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 913 and 4707.
2. (b) Morimoto, T.; Sekiya, M. Chem. Lett. 1985, 1371.
3. (c) Guanti, G.; Narisano, E.; Banfi, L. Tetrahedron Lett. 1987, 28, 4331 and 4335.
4. (d) Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397.
5. (e) Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889.
6. (f) Soga, T.; Takenoshita, H.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1990, 63, 3122.
7. (g) Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725.
8. (h) Onaka, M.; Ohno, R.; Yanagiya, N.; Izumi, Y. Synlett 1993, 141.
9. (i) Ishiara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963.
10. (j) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
11. (k) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773.
12. (l) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801.
13. 3 catalyzed allylation of imines see: (m) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (n) Cozzi, P. G.; Di Simone, B.; Umani-Ronchi, A. Tetrahedron Lett. 1996, 37, 1691.
14. 3 catalyzed allylation of imines see: (m) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289. (n) Cozzi, P. G.; Di Simone, B.; Umani-Ronchi, A. Tetrahedron Lett. 1996, 37, 1691.
15. Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O. Tetrahedron 1996, 52, 2573.
16. (a) Hirai, K.; Iwano, Y.; Mikoshiba, I.; Koyama, H.; Nishi, T. Heterocycles 1994, 38, 277.
17. (b) Hirai, K.; Homma, H.; Mikoshiba, I. Heterocycles 1994, 38, 281.
18. 3 does not promote the reaction between 2-pyridyl thioesters and imines.
19. 3 does not promote the reaction between 2-pyridyl thioesters and imines.
20. 3 does not promote the reaction between 2-pyridyl thioesters and imines.
21. 3 does not promote the reaction between 2-pyridyl thioesters and imines.
22. 3 is hygroscopic, its water content can increase.
23. cis = 5.0-6.0 Hz).
24. Kobayashi, S. Synlett 1994, 689.
25. 3 (see ref 5).
26. For a similar observation on the different reactivity of (E) and (Z) isomers of oxygenated SKTA see: Kobayashi, S.; Horibe, M.; Achiya, I. Tetrahedron Lett. 1993, 36, 3173 and references therein.
27. Imines of aromatic aldehydes are known to exist and react in the (E) configuration, while those of aliphatic aldehydes generally exist as mixtures of (E) and (Z) isomers. For a review see: McCarty, C. G. In The Chemistry of the C-N Double Bond; Patai, S., Ed.; Interscience: New York, 1970; Chapter 9, pp 363-464. Aromatic imines such as 6 were shown not to isomerize even in the presence of strong LA (see ref 4).
28. 2,12
29. Antiperiplanar transition states have been found to be preferred over their synclinal counterparts in an intramolecular LA-catalyzed aldol condensation: Denmark, S. E.; Lee, W. J. Org. Chem. 1994, 59, 707. Models analogous to A and B have been used to explain the stereoselectivity of Mukaiyama aldol condensation in general and of the aldol reaction of SKTA 1 in particular: Sun, K.-H.; Choo, D.-J. Tetrahedron Lett. 1995, 36, 6109. For a review see: Gennari, C. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Paart 2, Vol. 2, pp 629-660.
30. Antiperiplanar transition states have been found to be preferred over their synclinal counterparts in an intramolecular LA-catalyzed aldol condensation: Denmark, S. E.; Lee, W. J. Org. Chem. 1994, 59, 707. Models analogous to A and B have been used to explain the stereoselectivity of Mukaiyama aldol condensation in general and of the aldol reaction of SKTA 1 in particular: Sun, K.-H.; Choo, D.-J. Tetrahedron Lett. 1995, 36, 6109. For a review see: Gennari, C. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Paart 2, Vol. 2, pp 629-660.
31. Antiperiplanar transition states have been found to be preferred over their synclinal counterparts in an intramolecular LA-catalyzed aldol condensation: Denmark, S. E.; Lee, W. J. Org. Chem. 1994, 59, 707. Models analogous to A and B have been used to explain the stereoselectivity of Mukaiyama aldol condensation in general and of the aldol reaction of SKTA 1 in particular: Sun, K.-H.; Choo, D.-J. Tetrahedron Lett. 1995, 36, 6109. For a review see: Gennari, C. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Paart 2, Vol. 2, pp 629-660.
32. 4 addition of SKTA 1-3 to imines (see ref 2) should be ruled out.
33. NMR experiments (see ref 2) showed that (E)-SKTA 1-3 adopt this conformation in solution. For similar observations see: Wilcox, C. S.; Babston, R. E. J. Org. Chem. 1984, 49, 1451. Babston, R. E.; Lynch, V.; Wilcox, C. S. Tetrahedron Lett. 1989, 30, 447.
34. NMR experiments (see ref 2) showed that (E)-SKTA 1-3 adopt this conformation in solution. For similar observations see: Wilcox, C. S.; Babston, R. E. J. Org. Chem. 1984, 49, 1451. Babston, R. E.; Lynch, V.; Wilcox, C. S. Tetrahedron Lett. 1989, 30, 447.
35. 3SiCl see: Wang, D.-E.; Dai, X.-L.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649.
36. 3SiCl see: Wang, D.-E.; Dai, X.-L.; Hou, X.-L. Tetrahedron Lett. 1995, 36, 8649.
37. (a) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423.
38. (b) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195.
39. (c) Ishitani, H.; Nagayama, S. Kobayashi, S. J. Org. Chem. 1996, 61, 1902.
40. 3 the formation of imine 6 requires 3 h to occur at 60% yield at rt. As suggest by one of the reviewers, other possible scenarios involve imine fast formation and higher reactivity or a reversible SKTA additon to aldehydes and an irreversible one to imines.
41. In this synthesis of 11 the adduct derived from the condensation of nitromethane with imine 6 was obtained in 40% yield.
42. (19)β-Lactam 11t,c can be obtained from SKTA 1 and imine 6 in nitromethane also in the absence of the catalyst (two-component reaction: 22% yield; three-component reaction: 8% yield). An uncatalyzed Mukaiyama-Michael addition of a silyl ketene acetal to an unsaturated ketone in nitromethane has been previously reported: RajanBabu, V. T. J. Org. Chem. 1984, 49, 2083. The reaction of benzaldehyde with nitromethane rather than with a silyl ketene acetal in a Rh-catalyzed aldol process has been recently described: Kiyooka, S.-I.; Tsutui, T.; Maeda, H.; Kaneko, Y.; Isobe, K. Tetrahedron Lett. 1995, 36, 6531.
43. (19)β-Lactam 11t,c can be obtained from SKTA 1 and imine 6 in nitromethane also in the absence of the catalyst (two-component reaction: 22% yield; three-component reaction: 8% yield). An uncatalyzed Mukaiyama-Michael addition of a silyl ketene acetal to an unsaturated ketone in nitromethane has been previously reported: RajanBabu, V. T. J. Org. Chem. 1984, 49, 2083. The reaction of benzaldehyde with nitromethane rather than with a silyl ketene acetal in a Rh-catalyzed aldol process has been recently described: Kiyooka, S.-I.; Tsutui, T.; Maeda, H.; Kaneko, Y.; Isobe, K. Tetrahedron Lett. 1995, 36, 6531.
44. Annunziata, R.; Cinquini, M.; Cozzi, F.; Cozzi, P. G. J. Org. Chem. 1992, 57, 4155.
45. Kliegman, J. M.; Barnes, R. K. J. Org. Chem. 1970, 35, 3140.
46. For an example of the use of imine 21 in the synthesis of 4-formyl-substituted β-lactams see: Alcaide, B.; Martin-Cantalejo, Y.; Perez-Castells, J.; Rodriguez-Lopez, J.; Sierra, M. A.; Monge, A.; Perez-Garcia, V. J. Org. Chem. 1992, 57, 5921.
47. Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 109, 1129 and references cited therein. It must be noted that β-lactam 22c,a features the 3,3′-anti configuration and the functional groups required for the synthesis of the carbapenem antibiotics of the thienamycin family.
48. When this reaction was carried out in dichloromethane the yield was 64% and the c,s:t,s:c,a:t,a isomer ratio was 17:21:27:35. In acetonitrile, the yield was 46% and the isomer ratio 55:30:5:10.
49. The reactions of SKTA 2 with the N-4-(methoxyphenyl)imines derived from (S)-2-(benzyloxy)- and (S)-2-[(tert-butyldimethylsilyl)oxy]-propanal occurred in low yields (28 and 18%, respectively) and poor stereocontrol.
50. 3-catalyzed reaction described here.
51. 4-promoted stereoselective synthesis of β-lactams gave much more satisfactory results: see ref 20.
52. (a) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083.
53. (b) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11637.
54. Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71.
55. The first example of solid-phase combinatorial β-lactam synthesis has just been published: Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253. This method relies on a simple synthesis of imines immobilized on a polymeric matrix: Look, G. C.; Murphy, M. M.; Campbell, D. A.; Gallop, M. A. Tetrahedron Lett. 1995, 36, 2937.
56. The first example of solid-phase combinatorial β-lactam synthesis has just been published: Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253. This method relies on a simple synthesis of imines immobilized on a polymeric matrix: Look, G. C.; Murphy, M. M.; Campbell, D. A.; Gallop, M. A. Tetrahedron Lett. 1995, 36, 2937.