A study on the asymmetric synthesis of β-lactams through double stereodifferentiating cycloaddition reactions

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9186-9195

  Palomo, Claudio ^a   Aizpurua, Jesús M ^a   Mielgo, Antonia ^a   Linden, Anthony ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001012780     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9612180     Document Type: Article

References (78)

1. For some reviews on β-lactam antibiotics, see: (a) Dürkheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180. (b) Chemistry and Biology of β-Lactam Antibiotics, Vols. 1-3; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982. (c) Southgate, R.; Branch, C.; Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, p 621. (d) Southgate, R. Contemp. Org. Synth. 1994, 1, 417.
2. For some reviews on β-lactam antibiotics, see: (a) Dürkheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180. (b) Chemistry and Biology of β-Lactam Antibiotics, Vols. 1-3; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982. (c) Southgate, R.; Branch, C.; Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, p 621. (d) Southgate, R. Contemp. Org. Synth. 1994, 1, 417.
3. For some reviews on β-lactam antibiotics, see: (a) Dürkheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180. (b) Chemistry and Biology of β-Lactam Antibiotics, Vols. 1-3; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982. (c) Southgate, R.; Branch, C.; Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, p 621. (d) Southgate, R. Contemp. Org. Synth. 1994, 1, 417.
4. For some reviews on β-lactam antibiotics, see: (a) Dürkheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180. (b) Chemistry and Biology of β-Lactam Antibiotics, Vols. 1-3; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982. (c) Southgate, R.; Branch, C.; Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, p 621. (d) Southgate, R. Contemp. Org. Synth. 1994, 1, 417.
5. For comprehensive general reviews, see: (a) Koppel, G. A. In Small Ring Heterocycles; Hasner, A., Ed.; Wiley: New York, 1983; Vol. 42, p 219. (b) Backes, J. In Houben-Weyl, Methoden der Organischem Chemie; Muller, E., Bayer, O., Eds; Thieme: Stuttgart, 1991; Band E16B, p 31.
6. For comprehensive general reviews, see: (a) Koppel, G. A. In Small Ring Heterocycles; Hasner, A., Ed.; Wiley: New York, 1983; Vol. 42, p 219. (b) Backes, J. In Houben-Weyl, Methoden der Organischem Chemie; Muller, E., Bayer, O., Eds; Thieme: Stuttgart, 1991; Band E16B, p 31.
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8. For recent reviews on asymmetric synthesis of β-lactams, see: (a) Thomas, R. C. In Recent Progress in The Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; p 533. (b) Ternansky, R. J.; Morin, J. M., Jr. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 257. (c) Ghosez, L.; Marchand-Brynaert, S. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
9. For recent reviews on asymmetric synthesis of β-lactams, see: (a) Thomas, R. C. In Recent Progress in The Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; p 533. (b) Ternansky, R. J.; Morin, J. M., Jr. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 257. (c) Ghosez, L.; Marchand-Brynaert, S. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
10. For recent reviews on asymmetric synthesis of β-lactams, see: (a) Thomas, R. C. In Recent Progress in The Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; p 533. (b) Ternansky, R. J.; Morin, J. M., Jr. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 257. (c) Ghosez, L.; Marchand-Brynaert, S. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
11. For reviews on the asymmetric Staudinger reaction, see: (a) Cooper, R. D. G.; Daugherty, B. W.; Boyd, D. B. Pure Appl. Chem. 1987, 59, 485. (b) Van der Steen, F. H.; VanKoten, G. Tetrahedron 1991, 47, 5703. (c) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 295.
12. For reviews on the asymmetric Staudinger reaction, see: (a) Cooper, R. D. G.; Daugherty, B. W.; Boyd, D. B. Pure Appl. Chem. 1987, 59, 485. (b) Van der Steen, F. H.; VanKoten, G. Tetrahedron 1991, 47, 5703. (c) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 295.
13. For reviews on the asymmetric Staudinger reaction, see: (a) Cooper, R. D. G.; Daugherty, B. W.; Boyd, D. B. Pure Appl. Chem. 1987, 59, 485. (b) Van der Steen, F. H.; VanKoten, G. Tetrahedron 1991, 47, 5703. (c) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 295.
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22. (h) Palomo, C.; Aizpurua, J. M.; Legido, M.; Galarza, R.; Deya, P. M.; Dunogues, J.; Picard, J. P.; Ricci, A.; Seconi, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1239. For a new chiral aminoketene precursor, see:
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25. In general, the level of asymmetric induction achieved with imines derived from achiral aldehydes and chiral amines is lower than that for those derived from the ketene or aldehyde component. For example, see: (a) Georg, G. I.; Wu, Z. Tetrahedron Lett. 1994, 35, 381. For some exceptions, see: (b) Tenneson, S. M.; Belleau, B. Can. J. Chem. 1980, 58, 1605. (c) Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S.; Wagle, D. R. Tetrahedron 1992, 48, 4831. (c) Barton, D. H. R.; Gateau-Olesker, A.; Anaya-Mateos, J.; Cléophax, J.; Géro, S. D.; Chiaroni, A.; Riche, C. J. Chem. Soc., Perkin Trans. 1 1990, 3211. (d) Farina, V.; Hauck, S. I.; Walker, D. G. Synlett 1992, 761.
26. In general, the level of asymmetric induction achieved with imines derived from achiral aldehydes and chiral amines is lower than that for those derived from the ketene or aldehyde component. For example, see: (a) Georg, G. I.; Wu, Z. Tetrahedron Lett. 1994, 35, 381. For some exceptions, see: (b) Tenneson, S. M.; Belleau, B. Can. J. Chem. 1980, 58, 1605. (c) Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S.; Wagle, D. R. Tetrahedron 1992, 48, 4831. (c) Barton, D. H. R.; Gateau-Olesker, A.; Anaya-Mateos, J.; Cléophax, J.; Géro, S. D.; Chiaroni, A.; Riche, C. J. Chem. Soc., Perkin Trans. 1 1990, 3211. (d) Farina, V.; Hauck, S. I.; Walker, D. G. Synlett 1992, 761.
27. In general, the level of asymmetric induction achieved with imines derived from achiral aldehydes and chiral amines is lower than that for those derived from the ketene or aldehyde component. For example, see: (a) Georg, G. I.; Wu, Z. Tetrahedron Lett. 1994, 35, 381. For some exceptions, see: (b) Tenneson, S. M.; Belleau, B. Can. J. Chem. 1980, 58, 1605. (c) Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S.; Wagle, D. R. Tetrahedron 1992, 48, 4831. (c) Barton, D. H. R.; Gateau-Olesker, A.; Anaya-Mateos, J.; Cléophax, J.; Géro, S. D.; Chiaroni, A.; Riche, C. J. Chem. Soc., Perkin Trans. 1 1990, 3211. (d) Farina, V.; Hauck, S. I.; Walker, D. G. Synlett 1992, 761.
28. In general, the level of asymmetric induction achieved with imines derived from achiral aldehydes and chiral amines is lower than that for those derived from the ketene or aldehyde component. For example, see: (a) Georg, G. I.; Wu, Z. Tetrahedron Lett. 1994, 35, 381. For some exceptions, see: (b) Tenneson, S. M.; Belleau, B. Can. J. Chem. 1980, 58, 1605. (c) Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S.; Wagle, D. R. Tetrahedron 1992, 48, 4831. (c) Barton, D. H. R.; Gateau-Olesker, A.; Anaya-Mateos, J.; Cléophax, J.; Géro, S. D.; Chiaroni, A.; Riche, C. J. Chem. Soc., Perkin Trans. 1 1990, 3211. (d) Farina, V.; Hauck, S. I.; Walker, D. G. Synlett 1992, 761.
29. In general, the level of asymmetric induction achieved with imines derived from achiral aldehydes and chiral amines is lower than that for those derived from the ketene or aldehyde component. For example, see: (a) Georg, G. I.; Wu, Z. Tetrahedron Lett. 1994, 35, 381. For some exceptions, see: (b) Tenneson, S. M.; Belleau, B. Can. J. Chem. 1980, 58, 1605. (c) Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S.; Wagle, D. R. Tetrahedron 1992, 48, 4831. (c) Barton, D. H. R.; Gateau-Olesker, A.; Anaya-Mateos, J.; Cléophax, J.; Géro, S. D.; Chiaroni, A.; Riche, C. J. Chem. Soc., Perkin Trans. 1 1990, 3211. (d) Farina, V.; Hauck, S. I.; Walker, D. G. Synlett 1992, 761.
30. Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206.
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36. (d) Kobayashi, Y.; Takemoto, T.; Kamijo, T.; Harada, H.; Ito, Y.; Terashima, S. Tetrahedron 1992, 48, 1853. For related reactions using α,β-epoxy imines, see:
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41. For a recent paper dealing with the reaction of achiral ketenes with imines derived from chiral aldehydes and chiral amines, see: (a) Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (b) Niu, C.; Petterson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014.
42. For a recent paper dealing with the reaction of achiral ketenes with imines derived from chiral aldehydes and chiral amines, see: (a) Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (b) Niu, C.; Petterson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014.
43. For details on the mechanism of the Staudinger reaction, see: (a) ref 4a. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (b) Sordo, J. A.; González, J.; Sordo, T. L. J. Am. Chem. Soc. 1992, 114, 6249. (c) Palomo, C.; Cossío, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Cossío, F. P.; Ugalde, J. M.; López, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995. (e) Yamabe, S.; Minato, T.; Osamura, Y. J. Chem. Soc., Chem. Commun. 1993, 450.
44. For details on the mechanism of the Staudinger reaction, see: (a) ref 4a. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (b) Sordo, J. A.; González, J.; Sordo, T. L. J. Am. Chem. Soc. 1992, 114, 6249. (c) Palomo, C.; Cossío, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Cossío, F. P.; Ugalde, J. M.; López, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995. (e) Yamabe, S.; Minato, T.; Osamura, Y. J. Chem. Soc., Chem. Commun. 1993, 450.
45. For details on the mechanism of the Staudinger reaction, see: (a) ref 4a. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (b) Sordo, J. A.; González, J.; Sordo, T. L. J. Am. Chem. Soc. 1992, 114, 6249. (c) Palomo, C.; Cossío, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Cossío, F. P.; Ugalde, J. M.; López, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995. (e) Yamabe, S.; Minato, T.; Osamura, Y. J. Chem. Soc., Chem. Commun. 1993, 450.
46. For details on the mechanism of the Staudinger reaction, see: (a) ref 4a. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (b) Sordo, J. A.; González, J.; Sordo, T. L. J. Am. Chem. Soc. 1992, 114, 6249. (c) Palomo, C.; Cossío, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Cossío, F. P.; Ugalde, J. M.; López, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995. (e) Yamabe, S.; Minato, T.; Osamura, Y. J. Chem. Soc., Chem. Commun. 1993, 450.
47. For details on the mechanism of the Staudinger reaction, see: (a) ref 4a. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (b) Sordo, J. A.; González, J.; Sordo, T. L. J. Am. Chem. Soc. 1992, 114, 6249. (c) Palomo, C.; Cossío, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Cossío, F. P.; Ugalde, J. M.; López, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995. (e) Yamabe, S.; Minato, T.; Osamura, Y. J. Chem. Soc., Chem. Commun. 1993, 450.
48. For details on the mechanism of the Staudinger reaction, see: (a) ref 4a. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (b) Sordo, J. A.; González, J.; Sordo, T. L. J. Am. Chem. Soc. 1992, 114, 6249. (c) Palomo, C.; Cossío, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Cossío, F. P.; Ugalde, J. M.; López, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995. (e) Yamabe, S.; Minato, T.; Osamura, Y. J. Chem. Soc., Chem. Commun. 1993, 450.
49. For detailed information on this topic, see: (a) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755. (b) Ojima, I. Acc. Chem. Res. 1995, 383. (c) Hesse, M. In Ring enlargement in Organic Chemistry, VCH: Weinheim, 1991. (d) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299.
50. For detailed information on this topic, see: (a) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755. (b) Ojima, I. Acc. Chem. Res. 1995, 383. (c) Hesse, M. In Ring enlargement in Organic Chemistry, VCH: Weinheim, 1991. (d) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299.
51. For detailed information on this topic, see: (a) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755. (b) Ojima, I. Acc. Chem. Res. 1995, 383. (c) Hesse, M. In Ring enlargement in Organic Chemistry, VCH: Weinheim, 1991. (d) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299.
52. For detailed information on this topic, see: (a) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755. (b) Ojima, I. Acc. Chem. Res. 1995, 383. (c) Hesse, M. In Ring enlargement in Organic Chemistry, VCH: Weinheim, 1991. (d) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299.
53. For representative synthetic strategies to O-2-isocephems, see: (a) Tenneson, S. M.; Belleu, B. Can. J. Chem. 1980, 58, 1605. (b) Doyle, T. W.; Douglas, J. L.; Bellau, B.; Conway, T. T.; Ferrari, C. F.; Horning, D. E.; Lim, G.; Luh, B. Y.; Martel, A.; Menard, M.; Morris, M. L.; Misiek, M. Can. J. Chem. 1980, 58, 2508. (c) Hakimelahi, G. H. Helv. Chim. Acta 1982, 65, 1378. (d) Hrytsak, M.; Durst, T. Heterocycles 1987, 26, 2393. (e) Mastarelz, H.; Vinet, V. J. Chem. Soc., Chem. Commun. 1987, 1283. (f) Nitta, H.; Hatanaka, M.; Ishimura, T. J. Chem. Soc., Chem. Commun. 1987, 51. (g) Nitta, H.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Perkin Trans. 1 1990, 432. (h) Tsubouchi, H.; Tsuji, K.; Yasumura, K.; Tada, N.; Nishitami, S.; Minamikawa, J.; Ishikawa, H. Tetrahedron: Asymmetry 1994, 5, 441. See also ref 11b and references therein.
54. For representative synthetic strategies to O-2-isocephems, see: (a) Tenneson, S. M.; Belleu, B. Can. J. Chem. 1980, 58, 1605. (b) Doyle, T. W.; Douglas, J. L.; Bellau, B.; Conway, T. T.; Ferrari, C. F.; Horning, D. E.; Lim, G.; Luh, B. Y.; Martel, A.; Menard, M.; Morris, M. L.; Misiek, M. Can. J. Chem. 1980, 58, 2508. (c) Hakimelahi, G. H. Helv. Chim. Acta 1982, 65, 1378. (d) Hrytsak, M.; Durst, T. Heterocycles 1987, 26, 2393. (e) Mastarelz, H.; Vinet, V. J. Chem. Soc., Chem. Commun. 1987, 1283. (f) Nitta, H.; Hatanaka, M.; Ishimura, T. J. Chem. Soc., Chem. Commun. 1987, 51. (g) Nitta, H.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Perkin Trans. 1 1990, 432. (h) Tsubouchi, H.; Tsuji, K.; Yasumura, K.; Tada, N.; Nishitami, S.; Minamikawa, J.; Ishikawa, H. Tetrahedron: Asymmetry 1994, 5, 441. See also ref 11b and references therein.
55. For representative synthetic strategies to O-2-isocephems, see: (a) Tenneson, S. M.; Belleu, B. Can. J. Chem. 1980, 58, 1605. (b) Doyle, T. W.; Douglas, J. L.; Bellau, B.; Conway, T. T.; Ferrari, C. F.; Horning, D. E.; Lim, G.; Luh, B. Y.; Martel, A.; Menard, M.; Morris, M. L.; Misiek, M. Can. J. Chem. 1980, 58, 2508. (c) Hakimelahi, G. H. Helv. Chim. Acta 1982, 65, 1378. (d) Hrytsak, M.; Durst, T. Heterocycles 1987, 26, 2393. (e) Mastarelz, H.; Vinet, V. J. Chem. Soc., Chem. Commun. 1987, 1283. (f) Nitta, H.; Hatanaka, M.; Ishimura, T. J. Chem. Soc., Chem. Commun. 1987, 51. (g) Nitta, H.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Perkin Trans. 1 1990, 432. (h) Tsubouchi, H.; Tsuji, K.; Yasumura, K.; Tada, N.; Nishitami, S.; Minamikawa, J.; Ishikawa, H. Tetrahedron: Asymmetry 1994, 5, 441. See also ref 11b and references therein.
56. For representative synthetic strategies to O-2-isocephems, see: (a) Tenneson, S. M.; Belleu, B. Can. J. Chem. 1980, 58, 1605. (b) Doyle, T. W.; Douglas, J. L.; Bellau, B.; Conway, T. T.; Ferrari, C. F.; Horning, D. E.; Lim, G.; Luh, B. Y.; Martel, A.; Menard, M.; Morris, M. L.; Misiek, M. Can. J. Chem. 1980, 58, 2508. (c) Hakimelahi, G. H. Helv. Chim. Acta 1982, 65, 1378. (d) Hrytsak, M.; Durst, T. Heterocycles 1987, 26, 2393. (e) Mastarelz, H.; Vinet, V. J. Chem. Soc., Chem. Commun. 1987, 1283. (f) Nitta, H.; Hatanaka, M.; Ishimura, T. J. Chem. Soc., Chem. Commun. 1987, 51. (g) Nitta, H.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Perkin Trans. 1 1990, 432. (h) Tsubouchi, H.; Tsuji, K.; Yasumura, K.; Tada, N.; Nishitami, S.; Minamikawa, J.; Ishikawa, H. Tetrahedron: Asymmetry 1994, 5, 441. See also ref 11b and references therein.
57. For representative synthetic strategies to O-2-isocephems, see: (a) Tenneson, S. M.; Belleu, B. Can. J. Chem. 1980, 58, 1605. (b) Doyle, T. W.; Douglas, J. L.; Bellau, B.; Conway, T. T.; Ferrari, C. F.; Horning, D. E.; Lim, G.; Luh, B. Y.; Martel, A.; Menard, M.; Morris, M. L.; Misiek, M. Can. J. Chem. 1980, 58, 2508. (c) Hakimelahi, G. H. Helv. Chim. Acta 1982, 65, 1378. (d) Hrytsak, M.; Durst, T. Heterocycles 1987, 26, 2393. (e) Mastarelz, H.; Vinet, V. J. Chem. Soc., Chem. Commun. 1987, 1283. (f) Nitta, H.; Hatanaka, M.; Ishimura, T. J. Chem. Soc., Chem. Commun. 1987, 51. (g) Nitta, H.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Perkin Trans. 1 1990, 432. (h) Tsubouchi, H.; Tsuji, K.; Yasumura, K.; Tada, N.; Nishitami, S.; Minamikawa, J.; Ishikawa, H. Tetrahedron: Asymmetry 1994, 5, 441. See also ref 11b and references therein.
58. For representative synthetic strategies to O-2-isocephems, see: (a) Tenneson, S. M.; Belleu, B. Can. J. Chem. 1980, 58, 1605. (b) Doyle, T. W.; Douglas, J. L.; Bellau, B.; Conway, T. T.; Ferrari, C. F.; Horning, D. E.; Lim, G.; Luh, B. Y.; Martel, A.; Menard, M.; Morris, M. L.; Misiek, M. Can. J. Chem. 1980, 58, 2508. (c) Hakimelahi, G. H. Helv. Chim. Acta 1982, 65, 1378. (d) Hrytsak, M.; Durst, T. Heterocycles 1987, 26, 2393. (e) Mastarelz, H.; Vinet, V. J. Chem. Soc., Chem. Commun. 1987, 1283. (f) Nitta, H.; Hatanaka, M.; Ishimura, T. J. Chem. Soc., Chem. Commun. 1987, 51. (g) Nitta, H.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Perkin Trans. 1 1990, 432. (h) Tsubouchi, H.; Tsuji, K.; Yasumura, K.; Tada, N.; Nishitami, S.; Minamikawa, J.; Ishikawa, H. Tetrahedron: Asymmetry 1994, 5, 441. See also ref 11b and references therein.
59. For representative synthetic strategies to O-2-isocephems, see: (a) Tenneson, S. M.; Belleu, B. Can. J. Chem. 1980, 58, 1605. (b) Doyle, T. W.; Douglas, J. L.; Bellau, B.; Conway, T. T.; Ferrari, C. F.; Horning, D. E.; Lim, G.; Luh, B. Y.; Martel, A.; Menard, M.; Morris, M. L.; Misiek, M. Can. J. Chem. 1980, 58, 2508. (c) Hakimelahi, G. H. Helv. Chim. Acta 1982, 65, 1378. (d) Hrytsak, M.; Durst, T. Heterocycles 1987, 26, 2393. (e) Mastarelz, H.; Vinet, V. J. Chem. Soc., Chem. Commun. 1987, 1283. (f) Nitta, H.; Hatanaka, M.; Ishimura, T. J. Chem. Soc., Chem. Commun. 1987, 51. (g) Nitta, H.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Perkin Trans. 1 1990, 432. (h) Tsubouchi, H.; Tsuji, K.; Yasumura, K.; Tada, N.; Nishitami, S.; Minamikawa, J.; Ishikawa, H. Tetrahedron: Asymmetry 1994, 5, 441. See also ref 11b and references therein.
60. For representative synthetic strategies to O-2-isocephems, see: (a) Tenneson, S. M.; Belleu, B. Can. J. Chem. 1980, 58, 1605. (b) Doyle, T. W.; Douglas, J. L.; Bellau, B.; Conway, T. T.; Ferrari, C. F.; Horning, D. E.; Lim, G.; Luh, B. Y.; Martel, A.; Menard, M.; Morris, M. L.; Misiek, M. Can. J. Chem. 1980, 58, 2508. (c) Hakimelahi, G. H. Helv. Chim. Acta 1982, 65, 1378. (d) Hrytsak, M.; Durst, T. Heterocycles 1987, 26, 2393. (e) Mastarelz, H.; Vinet, V. J. Chem. Soc., Chem. Commun. 1987, 1283. (f) Nitta, H.; Hatanaka, M.; Ishimura, T. J. Chem. Soc., Chem. Commun. 1987, 51. (g) Nitta, H.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Perkin Trans. 1 1990, 432. (h) Tsubouchi, H.; Tsuji, K.; Yasumura, K.; Tada, N.; Nishitami, S.; Minamikawa, J.; Ishikawa, H. Tetrahedron: Asymmetry 1994, 5, 441. See also ref 11b and references therein.
61. Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
62. For a study on double asymmetric induction in the ester enolate-imine condensation, see: Annunziata, R.; Benaglia, M.; Chiovato, A.; Cinquini, M.; Cozzi, F. Tetrahedron 1995, 51, 10025.
63. Fisher, J. W.; Dunigan, J. M.; Hatfield, L. D.; Hoying, R. C.; Ray, J. E.; Thomas, K. L. Tetrahedron Lett. 1993, 34, 4755.
64. A semiempirical SCF-MO AM1 study carried out by us indicated that the stereochemistry observed for the reaction of chiral EvansSjogren ketenes with achiral imines, and particularly those involving the (trimethylsilyl)methyl moiety, is governed by the relative orientation adopted by the phenyl group in the corresponding transition state. While our theoretical work was in progress, an anticipated paper by Cossio from this laboratory documented the same observation, see: Cossío, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085.
65. 27
66. For some examples, see: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354. (b) Cardillo, G.; Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051. (c) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 515. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1991, 124, 2913.
67. For some examples, see: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354. (b) Cardillo, G.; Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051. (c) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 515. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1991, 124, 2913.
68. For some examples, see: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354. (b) Cardillo, G.; Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051. (c) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 515. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1991, 124, 2913.
69. For some examples, see: (a) Cardillo, G.; D'Amico, A.; Orena, M.; Sandri, S. J. Org. Chem. 1988, 53, 2354. (b) Cardillo, G.; Simone, A.; Gentilucci, L.; Sabatino, P.; Tomasini, C. Tetrahedron Lett. 1994, 35, 5051. (c) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Tetrahedron: Asymmetry 1992, 3, 515. (d) Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1991, 124, 2913.
70. Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res., Synop. 1992, 42.
71. 27
72. In this instance, the enamide I was also isolated. (Equation Presented)
73. (a) Ojima, I.; Suga, S.; Abe, R. Chem. Lett. 1980, 853.
74. (b) Alcaide, B.; Dominguez, G.; Escobar, G.; Parreno, M.; Plumet, J. Heterocycles 1986, 24, 1579.
75. (c) Thomas, R. C. Tetrahedron Lett. 1989, 46, 1579.
76. 4 positions, see: Cainelli, G.; Panunzio, M.; Bandini, E.; Martelli, G.; Spunta, G. Tetrahedron 1996, 52, 1685.
77. Farouz, F.; Miller, M. J. Tetrahedron Lett. 1991, 32, 3305.
78. The author has deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.