Mechanism of triflimide-catalyzed [3,3]-sigmatropic rearrangements of N-allylhydrazones—predictions and experimental validation

Chemical Science

Volumn 4, Issue 10, 2013, Pages 3997-4003

  Gutierrez, Osvaldo ^b   Thomson, Regan J ^a   Tantillo, Dean J ^b  

^a NORTHWESTERN UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL ANALYSIS; COMPUTATIONAL RESULTS; ELECTRON-DEFICIENT; EXPERIMENTAL VALIDATIONS; MILD REACTION CONDITIONS; SIGMATROPIC REARRANGEMENTS; STEREOGENIC CENTERS; TEMPERATURE DEPENDENCE;

FORECASTING;

CATALYSIS;

EID: 84883272379     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc51564h     Document Type: Article

References (26)

1. P. A. Wender, S. T. Handy, D. L. Wright, Chem. Ind., 1997, 765-769
2. I. S. Young, P. S. Baran, Nat. Chem., 2009, 1, 193-205
3. E. J. Corey and X.-M. Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989
4. K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem., Int. Ed., 2002, 41, 1668-1698
5. N. R. Candeias, F. Montalbano, P. M. S. D. Cal, P. M. P. Gois, Chem. Rev., 2010, 110, 6169-6193
6. A. Dömling, I. Ugi, Angew. Chem., Int. Ed., 2000, 39, 3168-3210
7. D. A. Mundal, J. J. Lee, R. J. Thomson, J. Am. Chem. Soc., 2008, 130, 1148-1149
8. D. A. Mundal, K. E. Lutz, R. J. Thomson, Org. Lett., 2009, 11, 465-468
9. K. E. Lutz, R. J. Thomson, Angew. Chem., Int. Ed., 2011, 50, 4437-4440
10. D. A. Mundal, K. E. Lutz, R. J. Thomson, J. Am. Chem. Soc., 2012, 134, 5782-5785
11. D. A. Mundal, C. A. Avetta Jr, R. J. Thomson, Nat. Chem., 2010, 2, 294-297
12. R. V. Stevens, E. E. McEntire, W. E. Barnett, E. Wenkert, J. Chem. Soc., Chem. Commun., 1973, 662-663
13. M. R. Siebert, D. J. Tantillo, Org. Lett., 2008, 10, 3219-3222
14. D. A. Hrovat, B. R. Beno, H. Lange, H.-Y. Yoo, K. N. Houk, W. T. Borden, J. Am. Chem. Soc., 1999, 121, 10529-10537
15. W. v. E. Doering, Y. Wang, J. Am. Chem. Soc., 1999, 121, 10967-10975
16. J. J. Blavins, D. L. Cooper, P. B. Karadakov, J. Phys. Chem. A, 2004, 108, 194-202
17. V. N. Staroverov, E. R. Davidson, J. Am. Chem. Soc., 2000, 122, 7377-7385
18. R. K. Hill, N. W. Gilman, Chem. Commun., 1967, 619-620
19. T. R. Hoye, D. O. Koltun, J. Am. Chem. Soc., 1998, 120, 4638-4643
20. G.-Q. Li, H. Gao, C. Keene, M. Devonas, D. H. Ess, L. Kürti, J. Am. Chem. Soc., 2013, 135, 7414-7417
21. S. Müller, M. J. Webber, B. List, J. Am. Chem. Soc., 2011, 133, 18534-18537
22. M. Rueping, A. P. Antonchick, Angew. Chem., Int. Ed., 2008, 47, 10090-10093
23. G. Jiménez-Osés, A. J. Brockway, J. T. Shaw, K. N. Houk, J. Am. Chem. Soc., 2013, 135, 6633-6642
24. Y. Liang, J. L. Mackey, S. A. Lopez, F. Liu, K. N. Houk, J. Am. Chem. Soc., 2012, 134, 17904-17907
25. R. L. Davis, C. A. Leverett, D. Romo, D. J. Tantillo, J. Org. Chem., 2011, 76, 7167-7174
26. L. Meng, S. Wang, J. C. Fettinger, M. J. Kurth, D. J. Tantillo, Eur. J. Org. Chem., 2009, 1578-1584