1,2-Migration in rhodium(II) carbene transfer reaction: Remarkable steric effect on migratory aptitude

Journal of Organic Chemistry

Volumn 71, Issue 15, 2006, Pages 5789-5791

  Xiao, Fengping ^a   Wang, Jianbo ^a  

^a Peking University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENES; DIAZO CARBONYL COMPOUNDS; ELECTRONIC EFFECT; STERIC EFFECT;

CHARGE TRANSFER; COMPLEXATION; DECOMPOSITION; ELECTROMIGRATION; REACTION KINETICS;

RHODIUM COMPOUNDS;

CARBENE; CARBONYL DERIVATIVE; DIAZO CARBONYL DERIVATIVE; RHODIUM; RHODIUM CARBENE; UNCLASSIFIED DRUG;

1,2 MIGRATION; ARTICLE; CHEMICAL REACTION KINETICS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

AZO COMPOUNDS; CATALYSIS; CHROMATOGRAPHY, THIN LAYER; ELECTRONICS; HYDROCARBONS; METHANE; MODELS, MOLECULAR; RHODIUM;

EID: 33746364845     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0605391     Document Type: Article

References (28)

1. For recent 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) Carbene Chemistry; Bertrand, G., Ed.; Fontis Media: Lausanne, Switzerland, 2002.
3. For 1,2-migration in rhodium(II) carbene, see the following. 1,2-Hydride migration: (a) Pellicciari, R.; Fringuelli, R.; Ceccherelli, P.; Sisani, E. J. Chem, Soc., Chem, Commun. 1979, 959-960.
4. (b) Ikota, N.; Takamura, N.; Young, S. D.; Ganem, B. Tetrahedron Lett. 1981, 22, 4163-4166.
5. (c) Hoffmann, K.-L.; Regitz, M. Tetrahedron Lett. 1983, 24, 5355-5358.
6. (d) Hudlicky, T.; Olivo, H. F.; Natchus, M. G.; Umpierrez, E. F.; Pandolfi, E.; Volonterio, C. J. Org. Chem. 1990, 55, 4767-4770.
7. (e) Taber, D. F.; Hoermer, R. S. J. Org. Chem. 1992, 57, 441-447.
8. (f) Ohno, M.; Itoh, M.; Umeda, M.; Furuta, R.; Kondo, K.; Eguchi, S. J. Am. Chem. Soc. 1996, 118, 7075-7082.
9. 1,2-Alkyl or 1,2-aryl migration: (g) Nagao, K.; Chiba, M.; Kim, S.-W. Synthesis, 1983, 197-199.
10. (h) Ye, T.; McKervey, M. A. Tetrahedron 1992, 48, 8007-8022.
11. (i) Kanemasa, S.; Kanai, T.; Araki, T.; Wada, E. Tetrahedron Lett. 1999, 40, 5055-5058.
12. 1,2-Acetoxy migration: (j) Lopez-Herrera, F. J.; Sarabia-Garcia F. Tetrahedron Lett. 1994, 35, 6705-6708.
13. (k) Lopez-Herrera, F. J.; Sarabia-Garcia, F. Tetrahedron 1997, 53, 3325-3346.
14. For reviews, see: (a) Nickon, A. Acc. Chem. Res, 1993, 26, 84-89.
15. (b) Liu, M. T. H. Acc. Chem. Res. 1994, 27, 287-294.
16. For recent study, see: (c) Farlow, R. A.; Thamattoor, D. M.; Sunoj, R. B.; Hadad, C. M. J. Org. Chem. 2002, 67, 3257-3265.
17. (d) Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Phys. Chem. A 1998, 102, 8467-8476.
18. (a) Jiang, N.; Qu, Z.; Wang, J. Org. Lett. 2001, 3, 2989-2992.
19. (b) Jiang, N.; Ma, Z.; Qu, Z.; Xing, X.; Xie, L.; Wang, J. J. Org Chem. 2003, 68, 893-900.
20. (c) Shi, W.; Jiang, N.; Zhang, S.; Wu, W.; Du, D.; Wang, J. Org. Lett. 2003, 5, 2243-2246.
21. (d) Shi, W.; Xiao, F.; Wang, J. J. Org. Chem. 2005, 70, 4318-4322.
22. (e) Xu, F.; Shi, W.; Wang, J. J. Org. Chem. 2005, 70, 4191-4194.
23. For the experimental details of the synthesis of 1a-f, 2a-e, and 3a-e and the characterization data for new compounds, see Supporting Information.
24. (a) Jiang, N.; Wang, J. Tetrahedron Lett. 2002, 43, 1285-1287.
25. (b) Bardot, V.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Tetrahedron: Asymmetry 1997, 8, 1111-1114.
26. Keating, A. E.; Garcia-Garibay, M. A.; Houk, K. N. J. Phys. Chem. A 1998, 102, 8467-8476.
27. For other examples in which the 1,2-migration is affected by steric/conformational factors, see: (a) Vitale, M.; Lecourt, T.; Sheldon, C. G.; Aggarwal, V. K. J. Am. Chem. Soc. 2006, 128, 2524-2525.
28. (b) Aggarwal, V. K.; Sheldon, C. G.; Macdonald, G. J.; Martin, W. P. J. Am. Chem. Soc. 2002, 124, 10300-10301.