New method for activation of aldimines in cycloaddition of lithium ynolates with N-2-methoxyphenyl imines leading to β-lactams

Tetrahedron Letters

Volumn 41, Issue 31, 2000, Pages 5943-5946

  Shindo, Mitsuru ^a   Oya, Soichiro ^a   Murakami, Ryoko ^a   Sato, Yusuke ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Azetidinones; Chelation; Imines; Ynolates

Indexed keywords

BETA LACTAM DERIVATIVE; IMINE; LITHIUM DERIVATIVE;

ARTICLE; CHELATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034730012     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00984-9     Document Type: Article

References (27)

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2. For reviews see: (a) Bloch, R. Chem. Rev. 1998, 98, 1407-1438. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. (c) Volkmann, R. A. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon: Oxford, 1991; Vol. 1, pp. 355-396. (d) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp. 975-1006.
3. For reviews see: (a) Bloch, R. Chem. Rev. 1998, 98, 1407-1438. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. (c) Volkmann, R. A. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon: Oxford, 1991; Vol. 1, pp. 355-396. (d) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp. 975-1006.
4. For reviews see: (a) Bloch, R. Chem. Rev. 1998, 98, 1407-1438. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. (c) Volkmann, R. A. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon: Oxford, 1991; Vol. 1, pp. 355-396. (d) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon: Oxford, 1991; Vol. 2, pp. 975-1006.
5. (a) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766.
6. (b) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232-233.
7. (c) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1997, 119, 10049-10053 and references therein.
8. For a review see: Shindo, M. Chem. Soc. Rev. 1998, 27, 367-374.
9. (a) Shindo, M. Tetrahedron Lett. 1997, 38, 4433-4436.
10. (b) Shindo, M.; Sato, Y.; Shishido, K. Tetrahedron 1998, 54, 2411-2422.
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13. Kai, H.; Iwamoto, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1996, 118, 7634-7635.
14. Shindo, M.; Oya, S.; Sato, Y.; Shishido, K. Heterocycles 1998, 49, 113-116.
15. A lanthanaid triflate activated cycloaddition of silyl ynol ether to 4-methoxyphenyl imines has been reported by us: Shindo, M.; Oya, S.; Sato, Y.; Shishido, K. Heterocycles 2000, 52, 545-548.
16. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
17. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
18. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
19. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
20. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
21. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
22. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
23. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
24. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
25. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
26. There have been many reports on stereocontrol of addition of organometallics to imines via chelation. Utilizing the N-2-hydroxyphenyl function, Kobayashi achieved high enantioselectivity and reaction acceleration in the asymmetric Mannich reaction and Strecker reaction: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 41, 7357-7360; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154; Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186-3188; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131-1132; Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432; Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545-546; Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161-2164; Kobayashi, S.; Kusakabe, K.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220-4221; Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225-1227; Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762-766. See also: Adrian Jr., J. C.; Barkin, J. L.; Hassib, L. Tetrahedron Lett. 1999, 40, 2457-2460.
27. Note added in proof: After submission of the revised manuscript, Yamamoto et al. reported the acceleration of addition of lithium ester enolates to N-2-methoxyphenyl aldimines: Saito, S.; Hatanaka, K.; Yamamoto, H. Org. Lett. 2000, 2, 1891-1894.