Silver-catalyzed ring-opening of cyclopropenes: Preparation of tertiary α-branched allylic amines

Tetrahedron

Volumn 69, Issue 27-28, 2013, Pages 5726-5731

  Phan, Diem T H ^b   Dong, Vy M ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

Branched allylic amines; Cyclopropenes; Hydroamination; Ring opening; Silver catalysis

Indexed keywords

AMINE; CYCLOPROPENE DERIVATIVE; PROPYLENE; SILVER; TERTIARY ALPHA BRANCHED ALLYLIC AMINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL; RING OPENING;

EID: 84878491247     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.04.133     Document Type: Article

References (31)

1. R.D. Bach, and O. Dmitrenko J. Am. Chem. Soc. 128 2006 4598
2. P.R. Khoury, J.D. Goddard, and W. Tam Tetrahedron 60 2004 8103
3. A. Fattahi, R.E. McCarthy, M.R. Ahmad, and S.R. Kass J. Am. Chem. Soc. 125 2003 11746
4. P.V.R. Schleyer, J.E. Williams, and K.R. Blanchard J. Am. Chem. Soc. 92 1970 2377
5. F.H. Allen Tetrahedron 38 1982 645 (f) Goering, B. K. Ph.D. Dissertation, Cornell University, 1995
6. Z.-B. Zhu, Y. Wei, and M. Shi Chem. Soc. Rev. 40 2011 5534
7. M. Rubin, M. Rubina, and V. Gevorgyan Chem. Rev. 107 2007 3117
8. I. Marek, S. Simaan, and A. Masarwa Angew. Chem., Int. Ed. 46 2007 7364
9. J.G. Buchanan, and H.Z. Sable B.S. Thyagarajan, Selective Organic Transformations Vol. 2 1972 Wiley-Interscience New York, NY 1 95
10. F. Miege, C. Meyer, and J. Cossy J. Org. Chem. 7 2011 714
11. F. Miege, C. Meyer, and J. Cossy Angew. Chem., Int. Ed. 50 2011 5932
12. F. Miege, C. Meyer, and J. Cossy Org. Lett. 12 2010 4144
13. M.S. Hadfiled, J.T. Bauer, P.E. Glen, and A.-L. Lee Org. Biomol. Chem. 8 2010 4090
14. C. Li, Y. Zeng, and J. Wang Tetrahedron Lett. 50 2009 2956
15. J.T. Bauer, M.S. Hadfield, and A.-L. Lee Chem. Commun. 2008 6405
16. Z.-B. Zhu, and M. Shi Chem. - Eur. J. 14 2008 10219
17. S. Chuprakov, and V. Gevorgyan Org. Lett. 9 2007 4463
18. A. Padwa, J.M. Kassir, and S.L. Xu J. Org. Chem. 62 1997 1642
19. A. Padwa, T.J. Blacklock, and R. Loza J. Am. Chem. Soc. 103 1981 2404
20. I. Nakamura, G.B. Bajracharya, and Y. Yamamoto J. Org. Chem. 68 2003 2297
21. X. Giner, and C. Najera Synlett 2009 3211
22. N. Krause, and N. Winter Chem. Rev. 111 2011 1994
23. A. Furstner Chem. Soc. Rev. 38 2009 3208
24. G. Seidel, R. Mynott, and A. Furstner Angew. Chem., Int. Ed. 48 2009 2510
25. D.N. Benitez, N.D. Shapiro, E. Tkatchouk, Y. Wang, W.A. Goddard III, and F.D. Toste Nat. Chem. 1 2009 482
26. M. Corral-Alvarez, M. Munoz-Dorado, and I. Garcia-Rodriguez Chem. Rev. 108 2008 3174
27. Y. Yamamoto Chem. Rev. 108 2008 3199
28. J.-M. Weibel, A. Blanc, and P. Pale Chem. Rev. 108 2008 3139
29. M. Harmata Silver in Organic Chemistry 2010 Wiley New Jersey, NJ
30. J. Lacour, and D. Moraleda Chem. Commun. 2009 7073
31. J. Lacour, and V. Hebbe-Vition Chem. Soc. Rev. 32 2003 373