2,3-Migration in Rh(II)-catalyzed reactions of β-trifluoroacetamido α-diazocarbonyl compounds

Organic Letters

Volumn 8, Issue 15, 2006, Pages 3207-3210

  Xu, Feng ^a   Zhang, Shiwei ^a   Wu, Xiangnan ^a   Liu, Yu ^a   Shi, Weifeng ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746898991     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061047d     Document Type: Article

References (37)

1. For comprehensive reviews, see: (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998.
2. (b) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1901.
3. 1,2-Hydrogen migration: (a) Frazen, V. Liebigs Ann. Chem. 1957, 602, 199.
4. (b) Pellicciari, R.; Fringuelli, R.; Ceccherelli, P.; Sisani, E. J. Chem. Soc., Chem. Commun. 1979, 959.
5. (c) Pellicciari, R.; Fringuelli, R.; Sisani, E. J. Chem. Soc., Perkin Trans. 1 1981, 2566.
6. (d) Hoffmann, K.-L.; Regitz, M. Tetrahedron Lett. 1983, 24, 5355.
7. (e) Hudlicky, T.; Olivo, H. F.; Natchus, M. G.; Umpierrez, E. F.; Pandolfi, E.; Volonterio, C. J. Org. Chem. 1990, 55, 4767.
8. (f) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57,441.
9. (g) Taber, D. F.; Hennessy, M. J.; Louey, J. P. J. Org. Chem. 1992, 57, 436.
10. (h) Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908.
11. (i) Sarabia García, F.; Pedraza Cebrián, G. M.; Heras López, A.; López Herrera, F. J. Tetrahedron 1998, 54, 6867.
12. (j) Ye, T.; McKervey, M. A. Tetrahedron 1992, 48, 8007.
13. 1,2-Aryl and 1,2-alkyl migrations: (a) Nagao, K.; Chiba, M.; Kim, S.-W. Synthesis 1983, 197.
14. (b) Kanemasa, S.; Kanai, T.; Araki, T.; Wada, E. Tetrahedron Lett. 1999, 40, 5055.
15. (c) Jiang, N.; Qu, Z.; Wang, J. Org. Lett. 2001, 3, 2989.
16. (d) Shi, W.; Jiang, N.; Zhang, S.; Wu, W.; Du, D.; Wang, J. Org. Lett. 2003, 5, 2243.
17. (e) Jiang, N.; Ma, Z.; Qu, Z.; Xing, X.; Xie, L.; Wang, J. J. Org. Chem. 2003, 68, 893.
18. (f) Aggarwal, V. K.; Sheldon, C. G.; Macdonald, G. J.; Martin, W. P. J. Am. Chem. Soc. 2002, 124, 10300.
19. 1,2-Thio group migration: (g) Xu, F.; Shi, W.; Wang, J. J. Org. Chem. 2005, 70, 4191.
20. 1,2-Vinyl and 1,2-acetylenyl migrations: (h) Shi, W.; Xiao, F.; Wang, J. J. Org. Chem. 2005, 70, 4318.
21. Very recently, a rare case of 1,2-alkyl migration that overrode 1,2-H migration has been reported; see: Vitale, M.; Lecourt, T.; Sheldon, C. G.; Aggarwal, V. K. J. Am. Chem. Soc. 2006, 128, 2524.
22. 2-Acetoxy migration: (a) Ikota, N.; Takamura, N.; Young, S. D.; Ganem, B. Tetrahedron Lett. 1981, 22, 4163.
23. (b) López-Herrera, F. J.; Sarabia-García, F. Tetrahedron Lett. 1994, 35, 6705.
24. (c) López-Herrera, F. J.; Sarabia-García, F. Tetrahedron 1997, 53, 3325.
25. Crich, D.; Yao, Q.; Filzen, G. F. J. Am. Chem. Soc. 1995, 117, 11455.
26. Shi, W.; Zhang, B.; Liu, B.; Xu, F.; Xiao, F.; Zhang, J.; Zhang, S.; Wang, J. Tetrahedron Lett. 2004, 45, 4563.
27. (b) Shi, W.; Zhang, B.; Zhang, J.; Liu, B.; Zhang, S.; Wang, J. Org. Lett. 2005, 7, 3103.
28. Jiang, N.; Wang, J. Tetrahedron Lett. 2002, 43, 1285.
29. Overman, L. E.; Owen, C. E.; Pavan, M. M.; Richards, C. J. Org. Lett. 2003, 5, 1809.
30. Uneyama, K.; Ohkura, H.; Hao, J.; Amii, H. J. Org. Chem. 2001, 66, 1026.
31. For X-ray structures, see the Supporting Information.
32. 2. The mixture was stirred for 5 h between 0 °C and room temperature. The solution was concentrated under reduced pressure, and the residue was subjected to chromatography on silica gel to afford the products 3a-1.
33. 2 was added dropwise at 0 °C over the course of 15 min. The reaction mixture was stirred until TLC analysis indicated the complete disappearance of the starting material (24 h). The solvent was then removed under reduced pressure, and the crude residue was purified by column chromatography to give the corresponding 2,3-migration products.
34. Xiao, F.; Wang, J. J. Org. Chem. 2006, 71, in press.
35. For examples of converting aldehydes to α-keto ester derivatives by two-carbon homologation, see: (a) Dalla, V.; Cotelle, P.; Catteau, J. P. Tetrahedron Lett. 1997, 38, 1577.
36. (b) Norman, B. H.; Kroin, J. S. J. Org. Chem. 1996, 61, 4990.
37. (c) Hanessian, S.; Mascitti, V.; Rogel, O. J. Org. Chem. 2002, 67, 3346.