Direct access to tetrahydro[1,2]diazepinones from α,β-epoxy-N- aziridinylimines via anionic rearrangement

Organic Letters

Volumn 15, Issue 4, 2013, Pages 914-916

  Wu, Fufang ^a,b,c   Dong, Min ^d   Fang, Fang ^b   Sang, Yingxia ^b   Li, Yun ^c   Cheng, Bin ^b,c   Zhang, Lihe ^d   Zhai, Hongbin ^c  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^c LANZHOU UNIVERSITY   (China)

^d SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE; AZIRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AZEPINES; AZIRIDINES; CYCLIZATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84873945615     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400070j     Document Type: Article

References (31)

1. Kirmse, W. Eur. J. Org. Chem. 1998, 201
2. Maruoka, K.; Oishi, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 2289
3. Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882
4. Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213
5. Lee, H.-Y.; Kim, D.-I.; Kim, S. Chem. Commun. 1996, 1539
6. Kim, S.; Cheong, J. H. Synlett 1997, 947
7. Kim, S.; Cheong, J. H.; Yoo, J. Synlett 1998, 981
8. Lee, H.-Y.; Kim, Y. J. Am. Chem. Soc. 2003, 125, 10156
9. Eschenmoser, A.; Felix, D.; Ohloff, G. Helv. Chim. Acta 1967, 50, 708
10. Schreiber, J.; Felix, D.; Eschenmoser, A.; Winter, M.; Gautschi, F.; Schulte-Elte, K. H.; Sundt, E.; Ohloff, G.; Kalvoda, J.; Kaufmann, H.; Wieland, P.; Anner, G. Helv. Chim. Acta 1967, 50, 2101
11. Tosylhydrazones were used instead. See: Tanabe, M.; Crowe, D. F.; Dehn, R. I.; Detre, G. Tetrahedron Lett. 1967, 8, 3739
12. Leone, C. L.; Chamberlin, A. R. Tetrahedron Lett. 1991, 32, 1691
13. Kim, S.; Cho, C. M.; Yoon, J.-Y. J. Org. Chem. 1996, 61, 6018
14. Kim, S.; Oh, D. H.; Yoon, J.-Y.; Cheong, J. H. J. Am. Chem. Soc. 1999, 121, 5330
15. Hwang, J.; Hong, Y.-T.; Kim, S. Adv. Synth. Catal. 2005, 347, 1513
16. Kim, S.; Hwang, J. Synlett 2010, 1511
17. Stevens, R. V.; Chang, J. H.; Lapalme, R.; Schow, S.; Schlageter, M. G.; Shapiro, R.; Weller, H. N. J. Am. Chem. Soc. 1983, 105, 7719
18. House, H. O.; Reif, D. J.; Wasson, R. L. J. Am. Chem. Soc. 1957, 79, 2490
19. Felix, D.; Muller, R. K.; Horn, U.; Joos, R.; Schreiber, J.; Eschenmoser, A. Helv. Chim. Acta 1972, 55, 1276
20. Kim, H. S.; Jeong, G.; Lee, H. C.; Kim, J. H.; Park, Y. T.; Okamoto, Y.; Kajiwara, S.; Kurasawa, Y. J. Heterocycl. Chem. 2000, 37, 1277
21. Ghavtadze, N.; Fröhlich, R.; Würthwein, E.-U. Eur. J. Org. Chem. 2009, 1228
22. Sherrill, R. G.; Berman, J. M.; Birkemo, L.; Croom, D. K.; Dezube, M.; Ervin, G. N.; Grizzle, M. K.; James, M. K.; Johnson, M. F.; Queen, K. L.; Rimele, T. J.; Vanmiddlesworth, F.; Sugg, E. E. Bioorg. Med. Chem. Lett. 2001, 11, 1145
23. Yadav, J. S.; Reddy, B. V. S.; Eshwaraiah, B.; Anuradha, K. Green Chem. 2002, 4, 592
24. Stroganova, T. A.; Butin, A. V.; Vasilin, V. K.; Nevolina, T. A.; Krapivin, G. D. Synlett 2007, 1106
25. Cope, A. C.; Tiffany, B. D. J. Am. Chem. Soc. 1951, 73, 4158
26. Eisch, J. J.; Galle, J. E. J. Am. Chem. Soc. 1976, 98, 4646
27. Eisch, J. J.; Galle, J. E. J. Org. Chem. 1990, 55, 4835
28. Capriati, V.; Florio, S.; Luisi, R.; Russo, V.; Salomone, A. Tetrahedron Lett. 2000, 41, 8835
29. Capriati, V.; Florio, S.; Luisi, R. Synlett 2005, 9, 1359
30. Capriati, V.; Florio, S.; Luisi, R. Chem. Rev. 2008, 108, 1918
31. Capriati, V.; Florio, S.; Salomone, A. In Topics in Stereochemistry; Siegel, J. S., Ed.; John Wiley & Sons: NewYork, 2010; Vol. 26, pp 135-164.