Substrate-dependent divergent outcomes from catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides: Azabicyclo[3.1.0]hexanes or 5-arylaminofuran-2(3 H)-ones

Journal of Organic Chemistry

Volumn 77, Issue 12, 2012, Pages 5313-5317

  Xu, Xinfang ^a   Shabashov, Dmitry ^a   Zavalij, Peter Y ^a   Doyle, Michael P ^a  

^a University of Maryland   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC REACTIONS; CATALYZED REACTIONS; DIPOLAR CYCLOADDITIONS; DIRHODIUM; NITRILE OXIDES;

CATALYSIS; CYCLOADDITION; HEXANE;

NITROGEN OXIDES;

5 ARYLAMINOFURAN 2 (3H)ONE DERIVATIVE; ACETIC ACID DERIVATIVE; BENZYL 4 METHYL 1 (2 NITROPHENYL) 3 OXO 2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; ENOL DIAZOACETATE DERIVATIVE; HEXANE; METHYL 1 (2 NITROPHENYL) 3 OXO 4 PHENYL 2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; METHYL 1 (4 ACETOXYPHENYL)3 OXO2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; METHYL 1 (4 BROMOPHENYL) 3 OXO 2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; METHYL 1 (4 CHLOROPHENYL) 3 OXO 2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; METHYL 1 (4 FLUOROPHENYL) 3 OXO 2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; METHYL 3 OXO 1 (2 (TRIFLUOROMETHYL)PHENYL) 2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; METHYL 3 OXO 1 (4 TOLYL) 2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; METHYL 4 METHYL 1 (2 NITROPHENYL) 3 OXO 2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; NITRILE OXIDE; TERT BUTYL 1 (2,4 DINITROPHENYL) 3 OXO 2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; TERT BUTYL 3 OXO 1 (2 (TRIFLUOROMETHYL)PHENYL) 2 OXA 6 AZABICYCLO[3.1.0]HEXANE 5 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; CYCLOADDITION; ISOMER; SILYLATION;

BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; FURANS; MOLECULAR STRUCTURE; NITRILES;

EID: 84862578731     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3006733     Document Type: Article

References (37)

1. Doyle, M. P.; McKervey, M. A.; Ye, T. In Modern CatalyticMethods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1998.
2. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704
3. Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857
4. Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861
5. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223
6. Selander, J. N.; Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 2477
7. Nadeau, E.; Ventura, D. L.; Brekan, J. A.; Davies, H. M. L. J. Org. Chem. 2010, 75, 1927
8. Qian, Y.; Xu, X.; Jiang, L.; Prajapati, D.; Hu, W. J. Org. Chem. 2010, 75, 7483
9. Cui, X.; Xu, X.; Lu, H.; Zhu, S.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 3304
10. Zhang, Z.; Liu, Y.; Ling, L.; Li, Y.; Dong, Y.; Gong, M.; Zhao, X.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 4330
11. Takeda, K.; Oohara, T.; Shimada, N.; Nambu, H.; Hashimoto, S. Chem.-Eur. J. 2011, 17, 13992
12. Weathers, T. M., Jr.; Wang, Y.; Doyle, M. P. J. Org. Chem. 2006, 71, 8183
13. Jaber, D. M.; Burgin, R. N.; Hepler, M.; Zavalij, P.; Doyle, M. P. Chem. Commun. 2011, 47, 7623
14. Doyle, M. P.; Ratnikov, M.; Liu, Y. Org. Biomol. Chem. 2011, 9, 4007
15. Xu, X.; Hu, W.; Doyle, M. P. Angew. Chem., Int. Ed. 2011, 50, 6392
16. Liu, Y.; Bakshi, K.; Zavalij, P. Y.; Doyle, M. P. Org. Lett. 2010, 12, 4304
17. Xu, X.; Hu, W.; Zavalij, P. Y.; Doyle, M. P. Angew. Chem., Int. Ed. 2011, 50, 11152
18. Qin, C.; Boyarskikh, V.; Hansen, J. H.; Hardcastle, K. I.; Musaev, D. G.; Davies, H. M. L. J. Am. Chem. Soc. 2011, 133, 19198
19. Lian, Y.; Davies, H. M. L. J. Am. Chem. Soc. 2011, 133, 11940
20. Lian, Y.; Hardcastle, K. I.; Davies, H. M. L. Angew. Chem., Int. Ed. 2011, 50, 9370
21. Davies, H. M. L.; Houser, J. H.; Thornley, C. J. Org. Chem. 1995, 60, 7529
22. Davies, H. M. L.; Ahmed, D.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774
23. Wang, X.; Xu, X.; Zavalij, P. J.; Doyle, M. P. J. Am. Chem. Soc. 2011, 133, 16402
24. Xu, X.; Ratnikov, M. O.; Zavalij, P. Y.; Doyle, M. P. Org. Lett. 2011, 13, 6122
25. Xu, X.; Shabashov, D.; Zavalij, P. Y.; Doyle, M. P. Org. Lett. 2012, 14, 800
26. Ueda, S.; Naruto, S.; Yoshida, T.; Sawayama, T.; Uno, H. J. Chem. Soc., Chem. Comm. 1985, 4, 218
27. Qi, X.; Jiang, Y.; Park, C. Chem. Commun. 2011, 47, 7848
28. Sakamoto, S.; Inokuma, T.; Takemoto, Y. Org. Lett. 2011, 13, 6374
29. Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640
30. Pereira, M. M. A.; Santos, P. P. In The Chemistry of Hydroxylamines, Oximes, and Hydroxamic Acids; Rappoport, Z.; Liebman, J. F., Eds.; Wiley-Interscience: Chichester, 2009; Chapter 9.
31. Davies, H. M. L.; Peng, Z.-Q.; Houser, J. H. Tetrahedron Lett. 1994, 35, 8939
32. Ueda, Y.; Roberge, G.; Vinet, V. Can. J. Chem. 1984, 62, 2936
33. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774
34. Schwartz, B. D.; Denton, J. R.; Lian, Y.; Davies, H. M. L.; Williams, C. M. J. Am. Chem. Soc. 2009, 131, 8329
35. Liu, K. C.; Shelton, B. R.; Howe, R. K. J. Org. Chem. 1980, 45, 3916
36. Larsen, K. E.; Torssel, K. B. G. Tetrahedron 1984, 40, 2985
37. Minakata, S.; Okumura, S.; Nagamachi, T.; Takeda, Y. Org. Lett. 2011, 13, 2966