Effective ring-opening reaction of aziridines with trimethylsilyl compounds: A facile access to β-amino acids and 1,2-diamine derivatives

Journal of Organic Chemistry

Volumn 65, Issue 5, 2000, Pages 1344-1348

  Wu, Jie ^a   Hou, Xue Long ^a   Dai, Li Xin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; BETA AMINO ACID; DIAMINE DERIVATIVE; TETRABUTYLAMMONIUM; TRIMETHYLSILYL DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 0034629504     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9913816     Document Type: Article

References (51)

1. (a) Hosomi, A.; Shirahata, A.; Sakurai, .Tetrahedron Lett. 1978, 19, 3043.
2. (b) Barker, T. K.; Andersen, N. H. Tetrahedron Lett. 1978, 19, 3513.
3. Deleris, G.; Dunogues, J.; Calas, R.; Pisciotti, F. J. Organomet. Chem. 1974,69, C 15.
4. Deleris, G.; Dunogues, J.; Galas, R.; Pisciotti, F. J. Organomet. Chem. 1975, 93, 43.
5. (e) Able, E. W.; Rowley, R. J. J. Organomet. Chem. 1975, 84, 199.
6. (f) Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976,1295.
7. (g) Generally, the Lewis acidcatalyzed allylation of carbonyl compound with allyl silane is known as the Sakurai-Hosomi reaction (Majetich suggested to name this reaction the Hosomi reaction; see: Majetich, G. In Organic Synthesis Theory and Application; Hudlicky, T., Ed.; JAI Press Ltd.: Greenwich, 1989; Vol. l, p 173. We further extended this name reaction also to the fluoride-triggered reaction.2
8. (h) Colvin, E. W. In Silicon Reagents in Organic Synthesis-(Best Synthetic Methods); Katritzky, A. R., MethCohn, O., Rees, C. W., Eds.; Academic Press Ltd.: London, 1988; p 1.
9. Wang, D.-K.; Zhou, Y.-G.; Tang, Y.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 1999, 64, 4233.
10. (a) Hudlicky, T.; Frazier, J. O.; Seoane, G.; Tiedje, M.; Seoane, A.;Kwart,L. D.;Beal,C. J. Am'. Chem. Soc. 1986,108,3755.
11. (b)Ploux, O.; Caruso, M.; Chassaing, G.; Marquet, A. J. Org. Chem. 1988, 53, 3154.
12. Satoh, T.; Sato, T.; Oohara, T.; Yamakawa, K J. Org. Chem.
13. 1989. 54, 3973.
14. Pearson, W. H.; Bergmeier, S. C.; Degan, S.; Lin, K.-C.; Poon, Y.-F.; Schkeryantz, J. M.; Williams, J. P. J. Org. Chem. 1990. 55, 5719.
15. (e) Hudlicky, T.; Luna, H.; Price, J. D.; Rulin, F. J. Org. Chem. 1990, 55, 4683.
16. (f) Hudlicky, T.; Fan, R.; Reed, J. W.; Gadamasetti, K. J. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, NY, 1992; Vol. 41, pp 151-124.
17. (g) Atkinson, R. S.; Coogan, M. P.; Cornell, C. L. J. Chem. Soc., Chem. Commun. 1993, 1215.
18. (h) Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 4349.
19. Davis, F. A.; Liu, H.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 5473.
20. For reviews of syntheses and reactions of activated and unactivated aziridines see: (a) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol.7, pp 47-93.
21. (b) Kasai, M.; Kono, M. Synlett 1992,778.
22. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
23. Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997,8,1693.
24. (e) Rayner, C. M. Synlett 1997, 11.
25. For example, see: (a) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998,27,13.
26. (b) Ibuka, T. Chem. Soc. Rev. 1998,27,145.
27. Stamm, H, J. Prakt. Chem. 1999, 341, 319.
28. Atkinson, R. S. Tetrahedron 1999, 55, 1519.
29. Leung, W. H.; Yu, M. T.; Wu, M. C.; Yeung, L. L. Tetrahedron Lett. 1996,37, 891.
30. Ferraris, D.; Drury, W. J., Ill; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568.
31. Matsubara, S.; Kodama, T.; Utimoto, K Tetrahedron Lett. 1990, 44, 6379.
32. Cantrill, A. A.; Osborn, H. M. I.; Sweeney, J. Tetrahedron 1998, 54, 2181.
33. Ohno, H.; Mori, A.; Inoue, S. Chem. Lett. 1993, 975.
34. (a) Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489.
35. (b) Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Chen, M.-B. J. Org. Chem. 1996, 61, 4641.
36. Zhou, Y.-G.; Li, A.-H.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1996, 1353.
37. Li, A.-H.; Zhou, Y.G.; Dai, L.-X.; Hou, X.-L.; Xia, L.-J.; Lin, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 1317.
38. (e) Hou, X.-L.; Yang, X.-K; Dai, L.-X.; Chen, X.-V Chant rnmmnn 1998 747
39. (a) Hou, X.-L.; Wu, J.; Dai, L.-X.; Xia, L.-J.; Tang, M.-H. Tetrahedron: Asymmetry 1998, 9, 1747.
40. (b) Hou, X.-L.; Wu, J.; Dai, L.-X. Chinese J. Chem. 1998,16, 557.
41. Wu, J.; Hou, X.-L.; Dai, L.X.; Xia, L.-J.; Tang, M.-H. Tetrahedron: Asymmetry 1998, 9, 3431.
42. Härtung, W. H.; Simonott, R. Org. React. 1953, VII, 263.
43. (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chetn. Soc 1998 120, 5315.
44. (b) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120.
45. (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am Chem Soc. 1994,116,2742.
46. (b) Zhang, Z.; Scheffold, R. Helv. Chim. Acta 1993 76,2602.
47. Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. Tetrahadron 1996, 52, 7817.
48. Bailly, C.; Houssin, R.; Dernier, J. L.; Henichart, J. P. Tetrahedron 1988, 44, 5833.
49. Chem. Abstr. 1990, 112, 157798v. Tanimoto, S.; Reddy, C. P.; Okamoto, T. Bull. Inst. Chem. Res., Kyoto University 1989, 66, 615.
50. Stamm, H.; Onistschenko, A.; Buchholz, B.; Mall, T. J. Org. Chem. 1989, 54, 193.
51. Qin, S.-Y.; Lu, Z.-F.; Li, J.-Z.; Liu, X.-M. Youji Huaxue (Chinese J. Org. Chem.) 1995, 15, 424.