Synthesis and functionalization of 3-alkylidene-1,2-diazetidines using transition metal catalysis

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1686-1689

  Brown, Michael J ^a   Clarkson, Guy J ^a   Inglis, Graham G ^b   Shipman, Michael ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE; AZETIDINE DERIVATIVE; COPPER; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; AZETIDINES; CATALYSIS; COPPER; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; STEREOISOMERISM;

EID: 79953204335     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200193n     Document Type: Article

References (34)

1. Singh, G. S. Mini Rev. Med. Chem. 2004, 4, 69
2. Singh, G. S. Mini Rev. Med. Chem. 2004, 4, 93
3. For a recent review, see: Burkhard, J. A.; Wuitschik, G.; Rogers-Evans, M.; Müller, K.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 9052
4. Feula, A.; Male, L.; Fossey, J. S. Org. Lett. 2010, 12, 5044
5. Ye, Y.; Wang, H.; Fan, R. Org. Lett. 2010, 12, 2802
6. Burkett, B. A.; Ting, S. Z.; Gan, G. C. S.; Chai, C. L. L. Tetrahedron Lett. 2009, 50, 6590
7. Hansen, C. P.; Jensen, A. A.; Christensen, J. K.; Balle, T.; Liljefors, T.; Frølund, B. J. Med. Chem. 2008, 51, 7380
8. Brandi, A.; Cicchi, S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988 and references cited therein
9. Che, Y.; Marshall, G. R. J. Org. Chem. 2004, 69, 9030
10. For a review, see: Lohray, B. B.; Bhushan, V. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon: New York, 1996; Vol. 1B, pp 911 - 968.
11. Kim, D. K.; O'Shea, K. E. J. Am. Chem. Soc. 2004, 126, 700
12. Paquette, L. A.; Webber, P.; Simpson, I. Org. Lett. 2003, 5, 177
13. Breton, G. W.; Shugart, J. H.; Hughey, C. A.; Perala, S. M.; Hicks, A. D. Org. Lett. 2001, 3, 3185
14. Abarca-Gonzalez, B.; Jones, R. A.; Medio-Simon, M.; Quiliz-Pardo, J.; Sepulveda-Arques, J.; Zaballos-Garcia, E. Synth. Commun. 1990, 20, 321
15. Cheng, C. C.; Seymour, C. A.; Petti, M. A.; Greene, F. D. J. Org. Chem. 1984, 49, 2910
16. Jensen, F.; Foote, C. S. J. Am. Chem. Soc. 1987, 109, 6376
17. Hall, J. H.; Jones, M. L. J. Org. Chem. 1983, 48, 822
18. Seymour, C. A.; Greene, F. D. J. Am. Chem. Soc. 1980, 102, 6384
19. Firl, J.; Sommer, S. Tetrahedron Lett. 1972, 13, 4713
20. Koerner von Gustorf, E.; White, D. V.; Kim, B.; Hess, D.; Leitich, J. J. Org. Chem. 1970, 35, 1155
21. Narayan, S.; Muldoon, J.; Finn, M. G.; Folkin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275 See also: Rieber, N.; Alberts, J.; Lipsky, J. A.; Lemal, D. M. J. Am. Chem. Soc. 1969, 91, 5668
22. Cheng, X.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 4581
23. Hall, J. H.; Bigard, W. S. J. Org. Chem. 1978, 43, 2785
24. Nelsen, S. F.; Peacock, V. E.; Weisman, G. R.; Landis, M. E.; Spencer, J. A. J. Am. Chem. Soc. 1978, 100, 2806
25. Brown, M. J.; Clarkson, G. J.; Fox, D. J.; Inglis, G. G.; Shipman, M. Tetrahedron Lett. 2010, 51, 382
26. For the efficient synthesis of other 4-membered ring systems by Cu-catalyzed ring closure, see: Lu, H.; Li, C. Org. Lett. 2006, 8, 5365
27. Fang, Y.; Li, C. J. Am. Chem. Soc. 2007, 129, 8092
28. Zhao, Q.; Li, C. Org. Lett. 2008, 10, 4037
29. Chen, L.; Shi, M.; Li, C. Org. Lett. 2008, 10, 5285
30. Zhao, Q.; Li, L.; Fang, Y.; Sun, D.; Li, C. J. Org. Chem. 2009, 74, 459
31. Dow, R. L.; Kelly, R. C.; Schletter, I.; Wierenga, W. Synth. Commun. 1981, 11, 43 This reaction is more commonly seen as an unwanted side reaction in conventional Mitsunobu reactions, see for example: Sammes, P. G.; Smith, S. J. Chem. Soc., Chem. Commun. 1983, 682
32. Gürtler, C.; Buchwald, S. L. Chem.-Eur. J. 1999, 5, 3107
33. Less strained 3-alkyl-1,2-diazetidines are known to be stable to Pd-catalyzed cross-coupling conditions, see ref 7.
34. Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924