Asymmetric synthesis of 2H-azirine carboxylic esters by an alkaloid-mediated Neber reaction

Journal of the American Chemical Society

Volumn 118, Issue 35, 1996, Pages 8491-8492

  Verstappen, Mariëlle M H ^a   Ariaans, Gerry J A ^a   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029790060     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961414o     Document Type: Article

References (42)

1. (a) Leonard, N. J.; Zwanenburg B. J. Am. Chem. Soc. 1967, 89, 4456-4465.
2. (b) Crist, D. R.; Leonard, N. J. Angew. Chem., Int. Ed. Engl. 1969, 8, 962-974.
3. For reviews on azirine chemistry, see: (a) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lowowski, W., Ed.; Pergamon Press: New York, 1984; Vol. 7, Chapter 5, p 47. (b) Nair, V. In Heterocyclic Compounds; Hassner A., Ed.; John Wiley and Sons: New York, 1983; Vol. 42.1, Chapter 2, pp 215-332.
4. For reviews on azirine chemistry, see: (a) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lowowski, W., Ed.; Pergamon Press: New York, 1984; Vol. 7, Chapter 5, p 47. (b) Nair, V. In Heterocyclic Compounds; Hassner A., Ed.; John Wiley and Sons: New York, 1983; Vol. 42.1, Chapter 2, pp 215-332.
5. For reviews on cycloadditions to azirines, see: (a) Anderson, D. J.; Hassner, A. Synthesis 1975, 483-495. (b) Hassner, A. Heterocycles 1980, 14, 1517-1528.
6. For reviews on cycloadditions to azirines, see: (a) Anderson, D. J.; Hassner, A. Synthesis 1975, 483-495. (b) Hassner, A. Heterocycles 1980, 14, 1517-1528.
7. Haddach, M.; Pastor, R.; Riess, J. G. Tetrahedron, 1993, 49, 4627-4638.
8. (a) Stapley, E. O.; Hendlin, D.; Jackson, M.; Miller, A. K. J. Antibiot. 1971, 24, 42-47.
9. (b) Miller, T. W.; Tristram, E. W.; Wolf, F. J. J. Antibiot. 1971, 24, 48-50.
10. Molinski, T. F.; Ireland, C. M. J. Org. Chem. 1988, 53, 2103-2105.
11. Salomon, C. E.; Williams, D. H.; Faulkner, D. J. J. Nat. Prod. 1995, 58, 1463-1466.
12. (a) Harvey, G. R.; Ratts, K. W. J. Org. Chem. 1966, 31, 3907-3910.
13. (b) Hassner, A.; Fowler, F. W. J. Am. Chem. Soc. 1968, 90, 2869-2875.
14. (c) Shin, C.; Yonezawa, Y.; Yoshimura, J. Chem. Lett. 1976, 1063-1066.
15. (d) Wade, T. N.; Guedj, R. Tetrahedron Lett. 1979, 3953-3954.
16. (a) Nishiwaki, T.; Kitamura, T.; Nakano, A. Tetrahedron 1970, 26, 453-465.
17. (b) Auricchio, S.; Vajna de Pava, O. J. Chem. Res. Synop. 1983, 132.
18. (c) Ueda, S.; Naruto, S.; Yoshida, T. Sawayama, T.; Uno, H. J. Chem Soc., Perkin Trans. 1 1988, 1013-1021.
19. Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 75-78.
20. Davis, F. A.; Reddy, G. V.; Liu, H. J. Am. Chem. Soc. 1995, 117, 3651-3652.
21. Gentilucci, L.; Grijzen, Y.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1995, 36, 4665-4668.
22. (a) Legters, J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 4881-4884.
23. (b) Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 1-15.
24. (c) Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243-3245.
25. Neber, P. W.; Burghard, A. Justus Liebigs Ann. Chem. 1932, 493, 281-294.
26. Cram, D. J.; Hatch, M. J. J. Am. Chem. Soc. 1953, 75, 33-38.
27. (a) Parcell, R. F. Chem. Ind. 1963, 1396-1397.
28. (b) Padwa, A.; Carlsen, P. H. J. J. Am. Chem. Soc. 1977, 99, 1514-1523.
29. (c) Müller, F.; Karwe, A.; Mattay, J. J. Org. Chem. 1992, 57, 6080-6082.
30. (d) Piskunova, I. P.; Eremeev, A. V.; Mishnev, A. F.; Vosekalna, I. A. Tetrahedron 1993, 49, 4671-4676.
31. O'Brien, C. Chem. Rev. 1964, 64, 81-89.
32. (a) Jacquier, R.; Petrus, C.; Petrus, F.; Verducci, J. Bull. Soc. Chim. Fr. 1970, 7, 2685-2690.
33. (b) Schulz, H.; Wakil, S. J. Anal. Biochem. 1970, 37, 457-461.
34. (c) Katritzky, A. R.; Barczynski, P.; Ostercamp, D. L.; Yousaf, T. I. J. Org. Chem. 1986, 51, 4037-4042.
35. 1H-NMR and GLC analyses).
36. 3N, but needed the stronger base tBuOK for its conversion in the corresponding azirine.
37. 4-protons.
38. Mopac 93, @ Fujitsu. Calculations performed with the AM1 Hamiltonian.
39. 4, and concentrated in vacuo to give the azirine ester 1. The crude product was purified by bulb-to-bulb distillation.
40. (a) Sziemies, G.; Mannhardt, K.; Junius, M. Chem. Ber. 1977, 110, 1792-1803.
41. (b) Gelas-Mialhe, Y.; Touraud, E.; Vessiere, R. Can. J. Chem. 1982, 60, 2830-2851.
42. The enantiopurity of the aziridine ester 2b was determined by GLC analysis of the camphanoyl derivative.