The S-thioester enolate/imine condensation: A shortcut to β-lactams

European Journal of Organic Chemistry

Volumn , Issue 4, 2000, Pages 563-572

  Benaglia, Maurizio ^a   Cinquini, Mauro ^a   Cozzi, Franco ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b NONE

Author keywords

5 Thioester; Enolate; Imine; Stereoselection; Lactams

Indexed keywords

ALUMINUM DERIVATIVE; BETA LACTAM DERIVATIVE; IMINE; ORGANOBORON DERIVATIVE; ORGANOMETALLIC COMPOUND; ORGANOTIN COMPOUND;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 0034006463     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200002)2000:4<563::aid-ejoc563>3.0.co;2-m     Document Type: Review

References (70)

1. For reviews see: [1a] D. J. Hart, D.-C. Ha, Chem. Rev. 1989, 89, 1447-1465.
2. [1b] M. J. Brown, Heterocycles 1989, 29, 2225-2244.
3. [1c] G. Cainelli, M. Panunzio, Il Farmaco 1991, 46, 177-190.
4. [1d] T. Fujisawa, M. Shimizu in Reviews on Heterocyclic Chemistry (Ed.: S. Oae), Myu, Tokyo, 1996, vol. 15, pp. 203-225.
5. H. Gilman, M. Speeter, J. Am. Chem. Soc. 1943, 65, 2255-2256.
6. On the other hand, the imine component of the reaction did not undergo relevant changes until the introduction of N-silylimines. For leading references see: G. Cainelli, D. Giacomini, P. Galletti, A. Gaiba, Synlett 1996, 657-658; and references cited therein.
7. For recent reports on the synthesis of S-thioesters see: [4a] T. Inoue, T. Takeda, N. Kambe, A. Ogawa, I. Ryu, N. Sonoda, J. Org. Chem. 1994, 59, 5824-5827.
8. [4b] A. L. Braga, O. E. D. Rodrigues, E. da Avila, C. C. Silveira, Tetrahedron Lett. 1998, 39, 3395-3396.
9. [4c] M. Yoshimatsu, M. Naito, M. Kawaigashi, H. Shimizu, T. Kataoka, J. Org. Chem. 1995, 60, 4798-4802.
10. [4d] W.-J. Xiao, G. Vasapollo, H. Alper, J. Org. Chem. 1998, 63, 2609-2612.
11. [4e] W.-J. Xiao, H. Alper, J. Org. Chem. 1998, 63, 7939-7944.
12. [4f] T.-C. Zheng, M. Burkart, D. E. Richardson, Tetrahedron Lett. 1999, 40, 603-606. References to previous works can be found in the reference lists of these papers.
13. M. W. Cronyn, M. P. Chang, R. A. Wall, J. Am. Chem. Soc. 1955, 77, 3031-3034.
14. K. T. Douglas, Acc. Chem. Res. 1986, 19, 186-192.
15. [7a] D. A. Evans, J. V. Nelson, T. R. Taber, J. Am. Chem. Soc. 1981, 103, 3099-3111.
16. [7b] C. Gennari, A. Bernardi, S. Cardani, C. Scolastico, Tetrahedron 1984, 40, 4059-4065.
17. [7c] H. C. Brown, R. K. Dhar, K. Ganesan, B. Singaram, J. Org. Chem. 1992, 57, 499-504.
18. M. Otsuka, M. Yoshida, S. Kobayashi, M. Ohno, Tetrahedron Lett. 1981, 22, 2109-2112.
19. T. Iimori, M. Shibasaki, Tetrahedron Lett. 1985, 26, 1523-1526.
20. S. Kobayashi, T. Iimori, T. Izawa, M. Ohno, J. Am. Chem. Soc. 1981, 103, 2406-2408.
21. T. Iimori, Y. Ishida, M. Shibasaki, Tetrahedron Lett. 1986, 27, 2149-2152.
22. T. Iimori, Y. Ishida, M. Shibasaki, Tetrahedron Lett. 1986, 27, 2153-2156.
23. M. Shibasaki, Y. Ishida, G. Iwasaki, T. Iimori, J. Org. Chem. 1987, 52, 3488-3489.
24. Strictly speaking, the α-methylbenzyl residue at the nitrogen in 10 cannot be regarded as a true chiral auxiliary, since its stereogenicity is destroyed upon reductive removal from the β-lactam. Nevertheless, we will use this term for these reagents throughout the text for simplicity and in agreement with common use.
25. This ring closure procedure was later improved by the use of copper(I) triflate: N. Miyachi, F. Kaneda, M. Shibasaki, J. Org. Chem. 1989, 54, 3511-3513.
26. For an improved synthesis of a precursor of (+)-PS-5 see: M. Mori, K. Kagechika, H. Sasai, M. Shibasaki, Tetrahedron 1991, 47, 531-540.
27. E. J. Corey, C. P. Decicco, R. C. Newbold, Tetrahedron Lett. 1991, 32, 5287-5290.
28. For another example of this process that involves ester see: K. Hattori, H. Yamamoto, Tetrahedron 1994, 50, 2785-2796.
29. T. Mukaiyama, H. Suzuki, T. Yamada, Chem. Lett. 1986, 915-918.
30. It was subsequently shown that the tin enolate of 14 was not formed by the addition of a tertiary amine to a mixture of S-thioester and tin(II) triflate: Y. Sugano, S. Naruta. Chem. Lett. 1989, 1331-1334.
31. T. Mukaiyama, H. Suzuki, T. Yamada, Chem. Lett. 1987, 293-296.
32. N. Yamasaki, M. Murakami, T. Mukaiyama, Chem. Lett. 1986, 1013-1016.
33. G. Iwasaki, M. Shibasaki, Tetrahedron Lett. 1987, 28, 3257-3260.
34. D. A. Evans, M. T. Bilodeau, T. C. Somers, J. Clardy, D. Cherry, Y. Kato, J. Org. Chem. 1991, 56, 5750-5752; and references cited therein.
35. R. Annunziata, M. Cinquini, F. Cozzi, P. G. Cozzi, E. Consolandi, Tetrahedron 1991, 47, 7897-7910.
36. The actual nature of these species is not known. For sake of simplicity they will be referred to and shown as trichlorotitanium enolates. The possibility that they exist as "ate" complexes and/or as polynuclear aggregates in solution has been suggested in ref.[24]
37. Several macrolactonization reactions took advantage of the "nucleofugacity" of the 2-pyridylthio group of an S-thioester. For a review on early work see: [27a] T. Mukaiyama, Angew. Chem. Int. Ed. Engl. 1976, 15, 94-103.
38. For recent examples of the use of 5-(2-pyridyl) thioesters in the formation of β-lactones see: [27b] G. Capozzi, S. Roelens, S. Talami, J. Org. Chem. 1993, 58, 7932-7936.
39. [27c] I. Arrestia, B. Lecea, F. P. Cossio, Tetrahedron Lett. 1996, 37, 245-248.
40. M. Cinquini, F. Cozzi, P. G. Cozzi, E. Consolandi, Tetrahedron 1991, 47, 8767-8774.
41. Introduction of substituents at positions 3 and 6 of the pyridine nucleus of the S-thioester was also studied: R. Annunziata, M. Cinquini, F. Cozzi, A. Lombardi Borgia, Gazz. Chim. Ital. 1993, 123, 181-184.
42. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, F. Ponzini, L. Raimondi, Tetrahedron 1994, 50, 2939-2948.
43. R. Annunziata, M. Cinquini, F. Cozzi, P. G. Cozzi, J. Org. Chem. 1992, 57, 4155-4162.
44. P. Andreoli, G. Cainelli, M. Panunzio, E. Bandini, G. Martelli, G. Spunta, J. Org. Chem. 1991, 56, 5984-5990.
45. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, F. Ponzini, J. Org. Chem. 1993, 58, 4746-4748.
46. Y. Kobayashi, Y. Takamoto, T. Kamijo, H. Harada, Y. Ito, S. Terashima, Tetrahedron 1992, 48, 1853-1868.
47. I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud, M. Zhao, Tetrahedron Lett. 1992, 33, 5737-5740.
48. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, L. Raimondi, Tetrahedron 1994, 50, 9471-9486.
49. R. Annunziata, M. Cinquini, F. Cozzi, L. Poletti, A. Perboni, B. Tamburini, Chirality 1998, 10, 91-94.
50. A. H. Berks Tetrahedron 1996, 52, 331-375.
51. J. Ngo, J. Castañer, Drugs of the Future 1996, 21, 1238-1243.
52. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, L. Poletti, L. Raimondi, A. Perboni, Eur. J. Org. Chem., in press.
53. C. Bolm, M. Ewald, M. Felder, G. Schlingloff, Chem. Ber. 1992, 125, 1169-1190.
54. M. Benaglia, M. Cinquini, F. Cozzi, unpublished results from these laboratories.
55. S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30.
56. R. Annunziata, M. Benaglia, A. Chiovato, M. Cinquini, F. Cozzi, Tetrahedron 1995, 51, 10025-10032.
57. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, L. Raimondi, Tetrahedron 1994, 50, 5821-5828.
58. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, O. Martini, V. Molteni, Tetrahedron 1996, 52, 2583-2590.
59. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, V. Molteni, L. Raimondi, Tetrahedron 1995, 51, 8941-8952.
60. V. K. Aggarwal, E. Andersen, R. Giles, A. Zaparucha, Tetrahedron: Asymmetry 1995, 6, 1301-1306.
61. T. Ishihara, K. Ichihara, H. Yamanake, Tetrahedron 1996, 52, 255-262.
62. K. Hirai, H. Homma, I. Mikoshiba, Heterocycles 1994, 38, 281-282.
63. R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, O. Schupp, Tetrahedron 1996, 52, 2573-2582. The use of the chiral Lewis acid boron trichloride/(1R,2S)-NME in the reaction of SKTA 98 with imine 44 led to a 58:42 mixture of azetidinones 51t and 51c, which were obtained in 50% and 24% ee., respectively.
64. R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, O. Schupp, J. Org. Chem. 1996, 61, 8293-8296.
65. S. Nagayama, S. Kobayashi, J. Org. Chem. 1997, 62, 232-233; and references cited therein.
66. R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, M. Benaglia, Tetrahedron Lett. 1998, 59, 1257-1260.
67. D. J. Gravert, K. D. Janda, Chem. Rev. 1997, 97, 489-505.
68. C. U. Kim, B. Luh, R. A. Partyka, Tetrahedron Lett. 1987, 28, 507-510.
69. K. Hirai, Y. Iwano, I. Mikoshiba, H. Koyama, T. Nishi, Heterocycles 1994, 38, 277-280.
70. P. Ramuzon, D. Bouzard, P. DiCesare, M. Essiz, J.-P. Jacquet, A. Nicolau, A. Martel, M. Menard, C. Bechaud, Tetrahedron 1995, 51, 9657-9670.