Diastereofacial selectivity in the reaction of chiral N-trimethylsilyl imines with ester enolates: Preparation of trans -azetidin-2-ones in high stereocontrolled fashion

Tetrahedron

Volumn 52, Issue 5, 1996, Pages 1685-1698

  Cainelli, Gianfranco ^a   Panunzio, Mauro ^a   Bandini, Elisa ^a   Martelli, Giorgio ^a   Spunta, Giuseppe ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030071117     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00997-3     Document Type: Article

References (103)

1. Gilman, H.; Specter, M. J. Am. Chem. Soc. 1943, 65, 2255.
2. (a) Hart, D.J.; Ha, D.C. Chem. Rev. 1989, 89, 1447.
3. (b) van Koten, G.; van der Steen, F.H.. Tetrahedron 1991, 47, 7503.
4. (c) Georg, I. G. "Studies in Natural Products Chemistry" ed. Rahman, A., Ed.; Elsevier Science: Amsterdam 1989, Vol. 4, p. 4331.
5. (c) Brown, M.J. Heterocycles 1989, 29, 2225.
6. Chemistry and Biology of β-Lactam Antibiotics; Morin R.B., Gorman, M.; Eds.; Academic Press: New York, 1982; Vol. 1-3
7. (a) Manhas, M.S.; Amiun, S.G.; Bose, A.K. Heterocycles 1976, 5, 699.
8. (b) Manhas, M.S.; Wagle, D.R.; Chiang, J.; Bose, A.K. Heterocycles, 1988, 27, 1755.
9. (a) Kagan, H.B.; Basselier, J.-J.; Luche, J.-L. Tetrahedron Lett. 1964, 941.
10. (b) Luche, J.-L.; Kagan, H.B. Bull. Soc. Chim. Fr. 1969, 3500.
11. (c) Luche, J.-L.; Kagan, H.B. Bull. Soc. Chim. Fr. 1971 2260.
12. (d) Dardoize, F.; Moreau, J.-L; Gaudemar, M. Bull. Soc. Chim. Fr. 1973, 1668. And Ref. therein cited.
13. Gluchowski, C.; Cooper, L.; Bergbreiter, D.E.; Newcomb, M. J. Org. Chem. 1980, 45, 3413.
14. (a) Andreoli, P.; Cainelli, G.; Contento, M.; Giacomini, D.; Martelli, G.; Panunzio, M. Tetrahedron Lett. 1986, 27, 1695.
15. (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Martelli, G. Spunta, G. Tetrahedron Lett. 1987, 27, 5369.
16. (c) Andreoli, P.; Cainelli, G.; Contento, M.; Giacomini, D.; Martelli, G.; Panunzio, M. J. Chem. Soc. Perkin 1, 1988, 945.
17. (d) Guillermin, J.C.; Ammi, L.; Denis, J.M. Tetrahedron Lett. 1988, 29, 1287.
18. (e) Uyehara, T.; Suzuki, I.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 4275.
19. (a) Ghosez, L.; Bogdan, S.; Ceresiat, M.; Frydrych, C.; Marchand-Brymaert, J.; Moya-Pottuguez, M.; Hubert, I. Pure Applied Chem. 1987, 59, 393.
20. (b) Marchand-Brynaert, J.; Moya-Portuguez, M.; Huber, I.; Ghosez, L. J. Chem. Soc. , Chem. Commun. 1983, 818.
21. (c) Belzecki, C.; Rogalska, E. J. Chem. Soc., Chem. Commun. 1981, 57.
22. (d) Rogalska, E.; Belzecki, C. J. Org. Chem. 1984, 49, 1397.
23. (a) Thomas, R.C. Tetrahedron Lett. 1989 30, 5239.
24. (b) Teutsch, G.; Bennet, A. Tetrahedron Lett. 1984, 25, 1561.
25. (c) Klich, M.; Teutsch, G. Tetrahedron, Lett. 1986, 42, 2677.
26. (d) Dugat, D.; Just, G.; Sahoo, S. Can. J. Chem. 1987, 65, 88.
27. (e) Gunda, T.E.; Vieth, S.; Kovér, K.E.; Sztaricskai, F. Tetrahedron Lett. 1990, 31, 6707.
28. (f) Aszodi, J.; Bonnet, A.; Teutsch, G.; Tetrahedron Lett. 1990, 46, 1579.
29. Furukawa, M.; Okawara, T.; Noguchi, Y.; Terawaki, Y.; Chem. Pharm. Bull. 1978, 26, 748.
30. Hart, D.J.; Lee, C.S.; Pirkle, W.H.; Hyon, M.H.; Tsipouras, A. J. Am. Chem. Soc. 1986, 108, 6054.
31. Oppolzer, W.; Chapuis, C.; Bernardinelli, G. Tetrahedron Lett. 1984, 25, 5885.
32. (a) Miller, R.W.J. Nat. Prod. 1980, 43, 425.
33. (b) Wani, M.C.; Taylor, H.L.; Wall, M.E.; Coggon, P.; McPhail, A.T. J. Am. Chem. Soc. 1971, 93, 2325.
34. (c) Gueritte-Voegelein, F.; Guenard, D.; Dubois, J.; Wahl, A.; Potier, P. La Chimica e Industria, 1994, 76, 490.
35. (a) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, H.Y.; Sun, M.C.; Brigaud, T. Tetrahedron, 1992, 48, 6985.
36. (b) Georg, I.G.; Cheruvallath, S.Z.; Harriman, B.C.G.; Hepperle, M.; Park, H. Bio. Med. Chem. Lett. 1993, 3, .2467.
37. (a) Perrone, E. and Franceschi, G. in Recent Progress in the Chemical Synthesis of Antibiotics Lukacs, G. and Ohno, M. Eds; Springer-Verlag Berlin 1990, pag. 615-703.
38. (b) Palomo, C. ibid, pp 565-612.
39. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729.
40. (d) Durckeimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K.H. Angew. Chem. Int. Ed. Engl. 1985, 24, 180.
41. For a three component approach to chiral 1β-methyl carbapenem see: (a) Tsukada, N.; Shimada, T.; Gyoung, Y.S.; Asao, N.; Yamamoto, Y. J. Org. Chem. 1995, 60, 143.
42. (b) Datta, A.; Georg, G.I. Chem Tracts, 1995, 7, 306 and references therein cited.
43. (a) Chiba, T.; Nagatsuma, M.; Nakai, T. Chem. Lett. 1984, 1927.
44. (b) Chiba, T.; Nakai, T. Chem. Lett. 1985, 651.
45. (c) Chiba, T.; Nagatsuma, M.; Nakai, T. Chem. Lett. 1985, 1343.
46. (d) Chiba, T.; Nakai, T. Tetrahedron Lett. 1985, 26, 4647.
47. (a) Hart, D.J.; Kanai, K.; Thomas, D.G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289.
48. (b) Hart, D.J.; Ha, D-C.; Yang, T.-K. J. Am. Chem. Soc. 1984, 106, 4819.
49. (c) Hart, D.J.; Ha, D.-C. Tetrahedron Lett. 1985, 5493.
50. (a) Georg, I.G.; Tetrahedron Lett. 1984, 25, 3779.
51. (b) Georg, I.G.; Gill, H.S.; Gerhardt, C. Tetrahedron Lett. 1985, 26, 3903.
52. (c) Georg, I.G.; Kant, J.; Gill, H.S. J. Am. Chem. Soc. 1987, 109, 1129.
53. (d) Georg, I.G.; Akgun, E. Tetrahedron Lett. 1990, 31, 3267.
54. (a) Iimori, T.; Shibasaki, M. Tetrahedron Lett. 1985, 26, 1523.
55. (b) Iimori, T.; Shibasaki, M. Tetrahedron Lett., 1986, 27, 2149.
56. (c) Iimori, T.; Ishida, Y.; Shibasaki, M. Tetrahedron Lett. 1986, 27, 2153.
57. (d) Mori, M.; Kagechika, K.; Tohjma, K.; Shibasaki, M. Tetrahedron Lett. 1988, 27,
58. (a) Cainelli, G.; Panunzio, M.; Basile, T.; Bongini, A.; Giacomini, D.; Martelli, G. J. Chem. Soc. Perkin 1, 1987, 2637.
59. (b) Cainelli, G.; Contento, M.; Giacomini, D.; Panunzio, M. Tetrahedron Lett., 1985, 26, 937.
60. Reviews on monobactams: Cimarusti, C.M.; Sykes, R.B. Chem. In Britain 1983, 302. Miller, M.J. Acc. Chem. Res. 1986, 44? 5553.
61. Reviews on monobactams: Cimarusti, C.M.; Sykes, R.B. Chem. In Britain 1983, 302. Miller, M.J. Acc. Chem. Res. 1986, 44? 5553.
62. Recent papers on the synthesis of monobactams: (a) Banfi, L.; Cascio, G.; Guanti, G.; Ghiron, C.; Manghisi, E.; Narisano, E.; Riva, R. Tetrahedron, 1995, 50, 11983 and Ref. cited.
63. (b) Teng, M.; Miller, M.J. J. Am. Chem. Soc. 1993, 115, 548.
64. (c) Brown, M.J.; Overman, L.E. J. Org. Chem. 1991, 56, 1933.
65. Furukawa, M.; Okawara, T.; Noguchi, Y.; Terawaki, Y. Chem. Pharm. Bull. 1978, 26, 260.
66. (a) Overman, L.E.; Brown, M.J. J. Org. Chem. 1991, 56, 1993.
67. (b) Overman, L.E.; Osawa, T. J. Am. Chem. Soc. 1985, 107, 1698.
68. (a) Cainelli, G.; Panunzio, M.; Giacomini, D.; Martelli, G.; Spunta, G.; Bandini, E: NATO-ASI "Chemical Synthesis: Gnosis and Prognosys" 1995, In Press.
69. (b) Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G.; Da Col, M. Tetrahedron 1995, 51, 5067.
70. (c) Panunzio, M.; Andreoli, P.; Martelli, G.; Spunta, G.; Giacomini, D.; Bandini, E. Pure and Applied Chem. 1990, 62, 605.
71. (d) Panunzio, M.; Giacomini, D.; Bandini, E. Seminars in Organic Synthesis S.C.I
72. (e) Bandini, E.; Cainelli, G.; Giacomini, D.; Martelli, G.; Panunzio, M.; Spunta, G. Biorganic and Medicinal Chem. Lett. 1993, 3, 2347.
73. (f) Bandini, E.; Cainelli, G.; Giacomini, D.; Martelli, G.; Panunzio, M.; Spunta, G. Gazz. Chim. It. 1993, 123, 509.
74. (g) Andreoli, P.; Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. J. Org. Chem., 1991, 56, 5984.
75. (h) Andreoli, P.; Billi, L.; Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. Tetrahedron. 1991, 47, 9061.
76. (i) Cainelli, G.; Panunzio, M. Il Farmaco, 1991, 46, 177.
77. (j) Cainelli, G.; Panunzio, M. Giacomini, D.; Martelli, G.; Spunta, G. J. Am. Chem. Soc. 1988, 110, 6879
78. Bernardi, F.; Bongini, A.; Cainelli, G.; Robb, M.A.; Suzzi Valli, G. J. Org. Chem. 1993, 58, 750.
79. Bongini, A.; Giacomini, D.; Panunzio, M.; Suzzi-Valli, G.; Zarantonello, P. Spectrochimica Acta 1995, 51A, 563.
80. Although we consider it unlikely under the reaction conditions used, reversible addition of Reformasky reagents to imines has been clearly established: (a) Dardoize, F.; Gaudemar, M. Bull. Soc. Chim. Fr. 1974, 939. See also Ref. 5.
81. For an excellent discussion of the possible transition state of ester-enolate-imine condensation see: Evans, D.A.; Nelson, J.V.; Taber, T.R.; Topics in Stereochemistry; Allinger, N.L., Eliel, E.L., S.H., Eds.; Wiley: New York, 1982; Vol. 13, pp 1-117
82. (a) Ireland, R.E.; Mueller, R.H.; Willard, A.K. J. Am. Chem. Soc. 1976, 98, 2868.
83. (b) Heathcook, C.H..; Buse, C.T.; Kleschick, W.A.; Pirrung, M.C.; Sohn, J.E.; Lampe, J. J. Org. Chem. 1980, 45, 1066.
84. (c) Seebach, D.; Amstutz, R.; Laube, T.; Schweizer, B.; Dunitz, J.D. J. Am. Chem. Soc. 1985, 107, 5403.
85. (d) van der Steen, F.H.; Boersma, J.; Spek, A.L.; van Koten, G. J. Organomet. Chem. 1990, 390, C21.
86. (e) van der Steen, F.H.; Boersma, J.; Spek, A.L.; van Koten, G. Organometallics 1991, 10, 2467.
87. The reaction of the zinc enolates have been extensively studied by van Koten et al., e.g., (a) van Maanen, H.L.; Kleijin, H.; Jastrzebski, J.T.B.H.; Lakin, M.T.; Spek, A.L.; van Koten, G. J. Org. Chem. 1994, 59, 7839.
88. (b) van der Steen, F.H.; Kleijn, HH.; Jastrzebski, J.T.B.H.; van Koten, G. J. Org. Chem. 1991, 56, 5147.
89. (c) van der Steen, F.H.; Kleijn, H.; Spek, A.L.; van Koten, G. J. Org. Chem. 1991, 56, 5868. The reaction of titanium enolates and thioesters has been elegantly developed by Cinquini, M. and Cozzi, F. See for example: (a) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Raimondi, L. Tetrahedron, 1994, 50, 9471.
90. (c) van der Steen, F.H.; Kleijn, H.; Spek, A.L.; van Koten, G. J. Org. Chem. 1991, 56, 5868. The reaction of titanium enolates and thioesters has been elegantly developed by Cinquini, M. and Cozzi, F. See for example: (a) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Raimondi, L. Tetrahedron, 1994, 50, 9471.
91. The generation of the imine by means of NaHMDSA gives rise to a diastereoselection comparable with that found using LiHMDSA. Nevertheless a faster imine formation and better yields in azetidinones are obtained with the latter one.
92. For simplicity sake only one enantiomer has been reported.
93. STABASE as protecting group: Djuric, S.; Venit, J.; Magnus, P. Tetrahedron Lett. 1981, 22, 1787.
94. See for example: Descases, J.; Luche, J.L.; Kagan, H.B. Tetrahedron Lett. 1975, 3661.
95. Reetz, M.T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556.
96. Concerning the influence of temperature and solvent on nucleophilic addition to N-(trimethylsilyl)imine of (2S)-lactal see: Cainelli, G.; Giacomini, D.; Walzl, M. Angew. Chem. In. Ed. 1995, 000. German Version: Angew. Chem. 1995, 107, 000.
97. Concerning the influence of temperature and solvent on nucleophilic addition to N-(trimethylsilyl)imine of (2S)-lactal see: Cainelli, G.; Giacomini, D.; Walzl, M. Angew. Chem. In. Ed. 1995, 000. German Version: Angew. Chem. 1995, 107, 000.
98. Shambayati, S.; Blake, F.J.; Wierschke, G.S.; Jorgensen, L.W.; Schreiber, L.S. J. Am. Chem. Soc. 1990, 112, 697.3,279-3,267*300=
99. (a) Chen, X.; Hortelano, E.R.; Eliel, E.L. J. Am. Chem. Soc. 1990, 112, 6130.
100. (b) Chen, X.; Hortelano, E.R.; Eliel, E.L.; Frye, S.V. J. Am. Chem. Soc. 1992, 114, 1778. For a up-to-date discussion on chelation controlled carbonyl addition see: Mori, S.; Nakamura, E.; Nakamura, M.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1995, 117, 5055.
101. (b) Chen, X.; Hortelano, E.R.; Eliel, E.L.; Frye, S.V. J. Am. Chem. Soc. 1992, 114, 1778. For a up-to-date discussion on chelation controlled carbonyl addition see: Mori, S.; Nakamura, E.; Nakamura, M.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1995, 117, 5055.
102. Leitereg, T. J.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 4019
103. The spectral data of the compounds 16c, 18c, 19c were superimposable with those of enantiomeric compounds 16b, 18b, and 19b (see Ref. 25f)