Finding reaction pathways for multicomponent reactions: The passerini reaction is a four-component reaction

Angewandte Chemie - International Edition

Volumn 50, Issue 3, 2011, Pages 644-649

  Maeda, Satoshi ^a,b   Komagawa, Shinsuke ^c,e   Uchiyama, Masanobu ^c,d   Morokuma, Keiji ^b  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c RIKEN   (Japan)

^d UNIVERSITY OF TOKYO   (Japan)

^e EMORY UNIVERSITY   (United States)

Author keywords

density functional calculations; multicomponent reactions; Passerini reaction; reaction mechanisms; transition states

Indexed keywords

DENSITY-FUNCTIONAL CALCULATIONS; MULTI-COMPONENT REACTIONS; PASSERINI REACTION; REACTION MECHANISM; TRANSITION STATE;

ALDEHYDES; CYANIDES; FORMIC ACID; KETONES;

DENSITY FUNCTIONAL THEORY;

ALDEHYDE; AMIDE; CARBOXYLIC ACID; CYANIDE; KETONE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALDEHYDES; AMIDES; CARBOXYLIC ACIDS; CYANIDES; KETONES;

EID: 78651395808     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201005336     Document Type: Article

References (34)

1. A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344
2. Angew. Chem. Int. Ed. 2000, 39, 3168-3210
3. D. J. Ramõn, M. Yus, Angew. Chem. 2005, 117, 1628-1661
4. Angew. Chem. Int. Ed. 2005, 44, 1602-1634
5. A. Dömling, Chem. Rev. 2006, 106, 17-89
6. D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature 2006, 441, 861-863
7. N. Elders, D. van der Born, L. J. D. Hendrickx, B. J. J. Timmer, A. Krause, E. Janssen, F. J. J. de Kanter, E. Ruijter, R. V. A. Orru, Angew. Chem. 2009, 121, 5970-5973
8. Angew. Chem. Int. Ed. 2009, 48, 5856-5859.
9. M. Passerini, L. Simone, Gazz. Chim. Ital. 1921, 51, 126-129
10. M. Passerini, L. Simone, Gazz. Chim. Ital. 1921, 51, 181-189
11. R. H. Baker, D. Stanonis, J. Am. Chem. Soc. 1951, 73, 699-702
12. R. Frey, S. G. Galbraith, S. Guelfi, C. Lamberth, M. Zeller, Synlett 2003, 1536-1538
13. U. Kusebauch, B. Beck, K. Messer, E. Herdtweck, A. Dömling, Org. Lett. 2003, 5, 4021-4024
14. P. R. Andreana, C. C. Liu, S. L. Schreiber, Org. Lett. 2004, 6, 4231-4233
15. M. A. Mironov, M. N. Ivantsova, M. I. Tokareva, V. S. Mokrushin, Tetrahedron Lett. 2005, 46, 3957-3960
16. X. Zeng, K. Ye, M. Lu, P. J. Chua, B. Tan, G. Zhong, Org. Lett. 2010, 12, 2414-2417
17. L. Kürti, B. Czakõ, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier B.V., Amsterdam, 2005.
18. N. Koga, K. Morokuma, Chem. Rev. 1991, 91, 823-842
19. S. Niu, M. B. Hall, Chem. Rev. 2000, 100, 353-405
20. T. Ziegler, J. Autschbach, Chem. Rev. 2005, 105, 2695-2722
21. K. N. Houk, P. H.-Y. Cheong, Nature 2008, 455, 309-313
22. U. Lourderaj, K. Park, W. L. Hase, Int. Rev. Phys. Chem. 2008, 27, 361-403.
23. K. Fukui, J. Phys. Chem. 1970, 74, 4161-4163
24. K. Ishida, K. Morokuma, A. Komornicki, J. Chem. Phys. 1977, 66, 2153-2156
25. M. Page, J. W. McIver, Jr., J. Chem. Phys. 1988, 88, 922-935
26. C. Gonzalez, H. B. Schlegel, J. Chem. Phys. 1989, 90, 2154-2161.
27. H. B. Schlegel, J. Comput. Chem. 2003, 24, 1514-1527
28. F. Jensen, Introduction to Computational Chemistry, 2 nd ed., Wiley, Chichester, 2007
29. D. J. Wales, Int. Rev. Phys. Chem. 2006, 25, 237-282.
30. S. Maeda, K. Morokuma, J. Chem. Phys. 2010, 132, 241102.
31. M. A. Collins, Theor. Chem. Acc. 2002, 108, 313-324.
32. A. Tachibana, K. Fukui, Theor. Chim. Acta 1978, 49, 321.
33. Y. Zhao, D. G. Truhlar, Acc. Chem. Res. 2008, 41, 157-167.
34. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999-3093.