Synthesis of optically active spiro-β-lactams by cycloadditions to α- alkylidene-β-lactams

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6369-6384

  Anklam, Sven ^a   Liebscher, Jürgen ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYLENE BETA LACTAM; BETA LACTAM DERIVATIVE; DIAZOMETHANE; DNA; SPIRO BETA LACTAM; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; DRUG SYNTHESIS; EPOXIDATION; OPTICAL ROTATION; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0032482308     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00296-8     Document Type: Article

References (38)

1. 1. Dürckheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem. Int. Ed. Engl. 1985, 24, 180-202.
2. 2. Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755-1802.
3. 3. a) Otto, H.-H.; Gürtler, S.; Ruf, S.; Johner, M. Pharmazie 1996, 51, 811-815;
4. b) Otto, H.-H.; Bergmann, H.-J.; Mayrhofer, R. Arch. Pharm. 1986, 319, 203-216;
5. c) Adlington, R. M.; Barrett, A. G. M.; Quayle, P.; Walker, A.; Betts, M. J. J. Chem. Soc. Perkin Trans 1 1983, 605-611;
6. d) Tanaka, K.; Yoda, H.; Inoue, K.; Kaji, A. Synthesis 1986, 66-69;
7. e) Kawashima, Y.; Sato, M.; Hatada, Y.; Goto, J.; Yamane, Y.; Hatayama, K. Chem. Pharm. Bull. 1991, 39, 3202-3206.
8. 4. a) Adam, S.; Arnold, W.; Schönholzer, P. Tetrahedron 1983, 39, 2485-2491.
9. b) Chen, Y. L.; Chang, C.-W.; Hedberg, K. Tetrahedron Lett. 1986, 27, 3449-3452.
10. c) Coulton, S.; Francois, I. J. Chem. Soc. Perkin Trans. 1 1991, 2699-2705;
11. d) Ohno, M.; Okano, K.; Kyotani, Y.; Ishihama, H.; Kobayashi, S. J. Am. Chem. Soc. 1983, 105, 7186-7187.
12. 5. a) Corbett, D. F. J. Chem. Soc. Perkin Trans. 1 1986, 421-428.
13. b) Häbich, D.; Metzger, K. Heterocycles 1986, 24, 289-296.
14. c) Guest, A. W.; Bateson, J. H. Tetrahedron Lett. 1993, 34, 1799-1802.
15. 6. Otto, H.-H.; Gürtler, S.; Johner, M.; Ruf, S. Helv. Chim. Acta 1993, 76, 2958-2968.
16. 7. Strauss, A.; Otto, H.-H. Helv. Chim. Acta 1997, 80, 1823-1830.
17. 8. The structure given in Fig. 3 of ref. 7 does not match with the text and the NOE results.
18. 9. Baldwin, J. E.; Otsuka, M.; Wallace, P. M. Tetrahedron 1986, 42, 3097-3110.
19. 10. Basak, A.; Bdour, H. M. M.; Bhattacharya, G. Tetrahedron Lett. 1997, 38, 2535-2538.
20. 11. Basak, A.; Mahato, T.; Bhattacharya, G.; Mukherjee, B. Tetrahedron Lett. 1997, 38, 643-646.
21. 12. a) Georg, G. I. Tetrahedron Lett. 1984, 25, 3779-3782.
22. b) Georg, G. I.; Gill, H. S.; Gerhardt, C. Tetrahedron Lett. 1985, 26, 3903-3906.
23. 13. Otto, H.-H.; Mayrhofer, R.; Bergmann, H.-J. Liebigs Ann. Chem. 1983, 1152-1161.
24. 14. Johnston, D. B. R.; Schmitt, S. M.; Bouffard, F. A.; Christensen, B. G. J. Am. Chem. Soc. 1978, 100, 313-315.
25. 15. Oshiro, Y; Agawa, T.; Ishida, M. Synthesis 1980, 933-935.
26. 16. Shibuya, M.; Jinbo, Y.; Kubota, S. Chem. Pharm. Bull. 1984, 32, 1303-1312.
27. 17. a) Seebach, D.; Peleties, N. Chem. Ber. 1972, 105, 511-520.
28. b) Hirai, K.; Fujimoto, K.; Iwano, Y. Bull. Chem. Soc. Jpn. 1986, 59, 1887-1896.
29. 18. Kende, A. S.; Liu, K.; Kaldor, I.; Dorey, G.; Koch, K. J. Am. Chem. Soc. 1995, 117, 8258-8270.
30. 19. Thomas, E. J.; Williams, A. C. J. Chem. Soc. Perkin Trans. 1 1995, 351-358.
31. 20. Howe, R. K.; Liu, K.-C.; Shelton, B. R. J. Org. Chem. 1980, 45, 3916-3918.
32. 21. For the generation of our spiroisoxazolidine 24 two transition states exo-E and endo-Z are suitable, while 6 would be the product of an opposite transition state, i.e. endo-E or exo-Z.
33. 22. Salzmann, T. N.; Ratcliffe, R. W.; Bouffard, F. A.; Christensen, B. G. J. Am. Chem. Soc. 1980, 102, 6161-6163.
34. 23. Kametani, T.; Huang, S.-P.; Yokohama, S.; Suzuki, Y.; Ihara, M. J. Am. Chem. Soc. 1980, 102, 2060-2065.
35. 24. deBoer, T. J.; Backer, H. J. Org. Synthesis, Coll. Vol. 4 1963, 250-253.
36. 25. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377-2377.
37. 26. Full details have been deposited at the Fachinformationszentrum Karlsruhe, 76344 Eggenstein-Leopoldshafen, Germany. This material can be obtained on quoting a full literature citation and deposition number CSD-408499.
38. 27. Full details have been deposited at the Fachinformationszentrum Karlsruhe, 76344 Eggenstein-Leopoldshafen, Germany. This material can be obtained on quoting a full literature citation and deposition number CSD-408500.