Tandem catalytic allylic amination and [2,3]-stevens rearrangement of tertiary amines

Journal of the American Chemical Society

Volumn 133, Issue 33, 2011, Pages 12956-12959

  Soheili, Arash ^a   Tambar, Uttam K ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC AMINATION; ALLYLIC SUBSTITUTION; CATALYST LOADINGS; DIASTEREOSELECTIVITIES; HIGH YIELD; MECHANISTIC STUDIES; MILD REACTION CONDITIONS; REARRANGEMENT REACTIONS; REVERSIBLE FORMATION; TERTIARY AMINE;

AMMONIUM COMPOUNDS; CATALYSIS; PALLADIUM; SUBSTITUTION REACTIONS;

AMINES;

ALLYLCARBONATE; AMINOESTER; AMMONIA; CARBONIC ACID; ESTER; NUCLEOPHILE; PALLADIUM; TERTIARY AMINE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; DIASTEREOSELECTIVITY; STEVENS REARRANGEMENT; SUBSTITUTION REACTION; TANDEM CATALYTIC ALLYLIC;

ALLYL COMPOUNDS; AMINATION; AMINES; CATALYSIS; ORGANIC CHEMISTRY PROCESSES; PALLADIUM;

EID: 80051779922     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja204717b     Document Type: Article

References (35)

1. Stevens, T. S.; Creigton, E. M.; Gordon, A. B.; MacNicol, M. J. Chem. Soc. 1928, 3193-3197
2. Markó, I. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 913-974.
3. Brückner, R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 6, pp 873-908.
4. Honda, K.; Inoue, S.; Sato, K. J. Am. Chem. Soc. 1990, 112, 1999-2001
5. Arboré, A. P. A.; Cane-Honeysett, D. J.; Coldham, I.; Middleton, M. L. Synlett 2000, 236-238
6. Vanecko, J. A.; Wan, H.; West, F. G. Tetrahedron 2006, 62, 1043-1062
7. Sweeney, J. B. Chem. Soc. Rev. 2009, 38, 1027-1038
8. Coldham, I.; Middleton, M. L.; Taylor, P. L. J. Chem. Soc., Perkin Trans. 1 1997, 2951-2952
9. Coldham, I.; Middleton, M. L.; Taylor, P. L. J. Chem. Soc., Perkin Trans. 1 1998, 2817-2821
10. Honda, K.; Tabuchi, M.; Kurokawa, H.; Asami, M.; Inoue, S. J. Chem. Soc., Perkin Trans. 1 2002, 1387-1396
11. Workman, J. A.; Garrido, N. P.; Sancüon, J.; Roberts, E.; Wessel, H. P.; Sweeney, J. B. J. Am. Chem. Soc. 2005, 127, 1066-1067
12. Gawley, R. E.; Moon, K. Org. Lett. 2007, 9, 3093-3096
13. Murata, Y.; Nakai, T. Chem. Lett. 1990, 2069-2072
14. Kessar, S. V.; Singh, P.; Singh, K. N.; Kaul, V. K.; Kumar, G. Tetrahedron Lett. 1995, 36, 8481-8484
15. Blid, J.; Somfai, P. Tetrahedron Lett. 2003, 44, 3159-3162
16. Blid, J.; Brandt, P.; Somfai, P. J. Org. Chem. 2004, 69, 3043-3049
17. Blid, J.; Panknin, O.; Somfai, P. J. Am. Chem. Soc. 2005, 127, 9352-9353
18. Blid, J.; Panknin, O.; Tuzina, P.; Somfai, P. J. Org. Chem. 2007, 72, 1294-1300
19. Somfai, P.; Panknin, O. Synlett 2007, 1190-1202
20. Doyle, M. P.; Tamblyn, W. H.; Bagheri, V. J. Org. Chem. 1981, 46, 5094-5102
21. Del Zotto, A.; Baratta, W.; Miani, F.; Verardo, G.; Rigo, P. Eur. J. Org. Chem. 2000, 3731-3735
22. Padwa, A.; Beall, L. S.; Eidell, C. K.; Worsencroft, K. J. J. Org. Chem. 2001, 66, 2414-2421
23. Clark, J. S.; Middleton, M. D. Tetrahedron Lett. 2003, 44, 7031-7034
24. Glaeske, K. W.; Naidu, B. N.; West, F. G. Tetrahedron: Asymmetry 2003, 14, 917-920
25. Zhou, C.-Y.; Yu, W.-Y.; Chan, P. W. H.; Che, C.-M. J. Org. Chem. 2004, 69, 7072-7082
26. Roberts, E.; Sancüon, J. P.; Sweeney, J. B. Org. Lett. 2005, 7, 2075-2078
27. Honda, K.; Shibuya, H.; Yasui, H.; Hoshino, Y.; Inoue, S. Bull. Chem. Soc. Jpn. 2008, 81, 142-147
28. Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689-1708
29. Hartwig, J. F.; Stanley, L. M. Acc. Chem. Res. 2010, 43, 1461-1475
30. Trost, B. M.; Zhang, T.; Sieber, J. D. Chem. Sci. 2010, 1, 427-440
31. Grellier, M.; Pfeffer, M.; van Koten, G. Tetrahedron Lett. 1994, 35, 2877-2880
32. van der Schaaf, P. A.; Sutter, J.-P.; Grellier, M.; van Mier, G. P. M.; Spek, A. L.; van Koten, G.; Pfeffer, M. J. Am. Chem. Soc. 1994, 116, 5134-5144
33. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595
34. Amatore, C.; Jutand, A.; Meyer, G.; Atmani, H.; Khalil, F.; Chahdi, F. O. Organometallics 1998, 17, 2958-2964
35. Murahashi, S.-I.; Imada, Y. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley-Interscience: New York, 2002; pp 1817-1825.