DFT study of brønsted acid catalyzed nitroso aldol reaction between achiral enamines and nitrosobenzene: The reason for regio- and enantioselectivity

European Journal of Organic Chemistry

Volumn , Issue 25, 2008, Pages 4245-4249

  Akakura, Matsujiro ^a   Kawasaki, Masanori ^b   Yamamoto, Hisashi ^b  

^a AICHI UNIVERSITY OF EDUCATION   (Japan)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

Density functional calculations; Enantioselectivity; Nitroso aldol reaction; Regioselectivity

Indexed keywords

EID: 53849083488     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800369     Document Type: Article

References (33)

1. For reviews o nitroso compounds, see: a) P. Zuman, P. Shah, Chem. Rev. 1994, 94, 1621-1641;
2. b) P. F. Vogt, M. J. Miller, Tetrahedron 1998, 54, 1317-1348;
3. for examples of (R)-aminoxylation and (R)-hydroxyamination to carbonyl compounds, see: c) T. Sasaki, K. Mori, M. Ohno, Synthesis 1985, 279;
4. d) T. Sasaki, K. Mori, M. Ohno, Synthesis 1985, 280;
5. e) W. Oppolzer, O. Tamura, G. Sundarababu, M. Signer, J. Am. Chem. Soc. 1992, 114, 5900-5902;
6. f) S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808-10809;
7. g) G. Zhong, Angew. Chem. Int. Ed. 2003, 42, 4247-4250;
8. h) Y. Hayashi, J. Yamaguchi, K. Hibino, M. Shoji, Tetrahedron Lett. 2003, 44, 8293-8296;
9. i) G. Zhong, Y. Yu, Org. Lett. 2004, 6, 1637-1639;
10. j) Y. Hayashi, J. Yamaguchi, T. Sumiya, M. Shoji, Angew. Chem. Int. Ed. 2004, 43, 1112-1115;
11. k) A. Bøgevig, H. Sundén, A. Córdova, Angew. Chem. Int. Ed. 2004, 43, 1109-1112;
12. l) N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2003, 125, 6038-6039;
13. m) N. Momiyama, H. Yamamoto, Angew. Chem. Int. Ed. 2002, 41, 2986-2986;
14. n) N. Momiyama, H. Yamamoto, Org. Lett. 2002, 4, 3579-3582;
15. o) N. Momiyama, H. Torii, S. Saito, H. Yamamoto, Proc. Natl. Acad. Sci. USA 2004, 101, 5374;
16. p) A. Córdova, H. Sundén, A. Bøgevig, M. Johansson, F. Himo, Chem. Eur. J. 2004, 10, 3673-3684;
17. q) N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5360-5361.
18. N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2005, 127, 1080-1081; also see the Supporting Information.
19. Paul Ha-Yeon Cheong, K. N. Houk, J. Am. Chem. Soc. 2004, 126, 13912-13913.
20. Acid-N was used for a complex in which the organic acid coordinates the nitrogen atom of the -N=O group and Acid-O-Z was used for a complex in which the organic acid coordinates the oxygen atom with a Z conformation. The Z conformation means that the Ph group and the organic acid part are on the same side relative to the N=O axis of the C-N=O plane. Acid-O-Z was more stable than Acid-O-E.
21. + complexes.
22. -) ion. See the Supporting Information.
23. Y. Chen, J. J. Dannenberg, J. Am. Chem. Soc. 2006, 128, 8100-8101.
24. The NPA charges of Acid-O-E suggest that a cooperative effect acts in the complexes arising from organic acids and PhNO. Detailed results of Acid-O-E are described in the Supporting Information.
25. The TS structures and ETS values of the reaction catalyzed by one molecule of an organic acid are described in the Supporting Information.
26. The total value of the energies of the enamine, PhNO, and two molecules of the organic acid was used as the standard for the relative energy level.
27. The nomenclature used for the TSs is as follows: the number indicates the type of bond forming (1 is C-N bond forming and 2 is C-O bond forming). The second character (m or a) refers to the catalyst (m is MeOH and a is AcOH). The third character (i or o) means the direction of the Ph group (i is inside and o is outside).
28. The energy gap written here is the one between the (R) and (S) TSs that is most stable among the reaction paths for each product. The other structures and relative energy levels are indicated in the Supporting Information.
29. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Gaussian, Inc., Pittsburgh, PA, 1998.
30. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J., J. A. Montgomery, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, K. Nakajima, Y. Honda, O. Kitao, H. Nakai, Li. X. Klene, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov; G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, revision C02, Gaussian, Inc., Pittsburgh, PA, 2003.
31. a) A. D. Becke, J. Chem. Phys. 1993, 96, 5648;
32. b) P. J. Stevens, J. F. Devlin, C. F. Chablowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
33. S. F. Boys, F. Bernardi, Mol. Phys. 1970, 19, 553.