The formal [4+3] cycloaddition between donor-acceptor cyclobutanes and nitrones

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1528-1531

  Stevens, Andrew C ^a   Palmer, Cory ^a   Pagenkopf, Brian L ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952594276     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200220d     Document Type: Article

References (40)

1. For reviews see: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; John Wiley & Sons, Inc.: New York, 2002.
2. Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887-2902
3. For recent examples see: Sumiya, T.; Ishigami, K.; Wantanabe, H. Angew. Chem., Int. Ed. 2010, 49, 5527-5528
4. Creech, G. S.; Kwon, O. J. Am. Chem. Soc. 2010, 132, 8876-8877
5. Repka, L. M.; Ni, J.; Reisman, S. E. J. Am. Chem. Soc. 2010, 132, 14418-14420
6. Spiteri, C.; Kelling, S.; Moses, J. E. Org. Lett. 2010, 12, 3368-3371
7. Gryko, D. T.; Rogacki, M. K.; Klajn, J.; Gałezowski, M.; Stepień, K.; Cyrański, M. K. Org. Lett. 2010, 12, 2020-2023
8. For reviews see: Tufariello, J. J. Acc. Chem. Res. 1979, 12, 396-403
9. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909
10. Denmark, S. E.; Cottell, J. J. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., Eds.; John Wiley & Sons: New York, 2003.
11. Kinugasa, M.; Hashimoto, S. J. Chem. Soc., Chem. Commun. 1972, 466-467
12. Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572-4573
13. Zhang, X.; Hsung, R. P.; Li, H.; Zhang, Y.; Johnson, W. L.; Figueroa, R. Org. Lett. 2008, 10, 3477-3479
14. Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119-3121
15. Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023-3026
16. Young, I. S.; Kerr, M. A. Org. Lett. 2004, 6, 139-141
17. Ganton, M. D.; Kerr, M. A. J. Org. Chem. 2004, 69, 8554-8557
18. For reviews see: Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73-135
19. Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196
20. Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321-347
21. Carson, C. A.; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051-3060
22. De Simone, F.; Waser, J. Synthesis 2009, 20, 3353-3374
23. Wiberg, K. B. The Chemistry of Cyclobutanes, Part I; Rappoport, Z.; Liebman, J. F., Eds.; John Wiley & Sons Ltd: Chichester, England, 2005; pp 4 - 5.
24. Shimada, S.; Saigo, K.; Nakamura, H.; Hasegawa, M. Chem. Lett. 1991, 20, 1149-1152
25. Matsuo, J.-I.; Sasaki, S.; Tanaka, H.; Ishibashi, H. J. Am. Chem. Soc. 2008, 130, 11600-11601
26. Parsons, A. T.; Johnson, J. S. J. Am. Chem. Soc. 2009, 131, 14202-14203
27. Allart, E. A.; Christie, S. D. R.; Pritchard, G. J.; Elsegood, M. R. Chem. Commun. 2009, 47, 7339-7341
28. Moustafa, M. M. A. R.; Stevens, A. C.; Machin, B. P.; Pagenkopf, B. L. Org. Lett. 2010, 12, 4736-4738
29. Negishi, S.; Ishibashi, H.; Matsuo, J.-I. Org. Lett. 2010, 12, 4984-4987
30. Matsuo, J.-I.; Okado, R.; Ishibashim, H. Org. Lett. 2010, 12, 3266-3268
31. Moustafa, M. M. A. R.; Pagenkopf, B. L. Org. Lett. 2010, 12, 4732-4735
32. Matsuo, J.-I.; Negishi, S.; Ishibashi, H. Tetrahedron Lett. 2009, 50, 5831-5833
33. Matsuo, J.-I.; Sasaki, S.; Hoshikawa, T.; Ishibashi, H. Org. Lett. 2009, 11, 3822-3825
34. Oxazepines have been made by the reaction of 1-(1-alkynyl) cyclopropyl ketones with nitrones: Zhang, Y.; Liu, F.; Zhang, J. Chem.-Eur. J. 2010, 16, 6146-6150
35. Kurihara, T.; Sakamoto, Y.; Kimura, T.; Ohishi, H.; Harusawa, S.; Yoneda, R.; Suzutani, T.; Azuma, M. Chem. Pharm. Bull. 1996, 44, 900-908
36. van Maarseveen, J. H.; Scheeren, H. W.; De Clercq, E.; Balzarini, J.; Kruse, C. G. Bioorg. Med. Chem. 1997, 5, 955-970
37. Hu, B.; Zhu, J.; Xing, S.; Fang, J.; Du, D.; Wang, Z. Chem.-Eur. J. 2009, 15, 324-327
38. Wu, L.; Shi, M. Chem.-Eur. J. 2010, 16, 1149-1152
39. 4 Å molecular sieves were needed to prevent hydrolysis of the nitrone.
40. A mixture of three diastereomers was formed, cis: trans:third 1.0:1.4:1.4, 95% yield.