Enantioselective Michael additions of nitromethane by a catalytic double activation method using chiral Lewis acid and achiral amine catalysts

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13394-13395

  Itoh, Kennosuke ^a   Kanemasa, Shuji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; LEWIS ACID; NITROMETHANE; PYRAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY;

EID: 0037073238     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027313+     Document Type: Article

References (39)

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2. Micheal additions of malonates: (a) End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem. Eur. J. 1988, 4, 818-824. Nitro-Mannich reactions: (b) Nishiwaki, N.; Knudsen, K. R.; Gothelf, K. V.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2992-2995. Nitro aldol reactions: (c) Trost, B. M.; Yeh, V. S. C. Angew Chem., Int. Ed. 2002, 41, 861-863. (d) Shibasaki, M.; Sasai, H.; Arai, T. Angew Chem., Int. Ed. Engl. 1997, 36, 1236-1256. Thiol conjugate additions: (e) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417-430.
3. Micheal additions of malonates: (a) End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem. Eur. J. 1988, 4, 818-824. Nitro-Mannich reactions: (b) Nishiwaki, N.; Knudsen, K. R.; Gothelf, K. V.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2992-2995. Nitro aldol reactions: (c) Trost, B. M.; Yeh, V. S. C. Angew Chem., Int. Ed. 2002, 41, 861-863. (d) Shibasaki, M.; Sasai, H.; Arai, T. Angew Chem., Int. Ed. Engl. 1997, 36, 1236-1256. Thiol conjugate additions: (e) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417-430.
4. Micheal additions of malonates: (a) End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem. Eur. J. 1988, 4, 818-824. Nitro-Mannich reactions: (b) Nishiwaki, N.; Knudsen, K. R.; Gothelf, K. V.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2992-2995. Nitro aldol reactions: (c) Trost, B. M.; Yeh, V. S. C. Angew Chem., Int. Ed. 2002, 41, 861-863. (d) Shibasaki, M.; Sasai, H.; Arai, T. Angew Chem., Int. Ed. Engl. 1997, 36, 1236-1256. Thiol conjugate additions: (e) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417-430.
5. Micheal additions of malonates: (a) End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem. Eur. J. 1988, 4, 818-824. Nitro-Mannich reactions: (b) Nishiwaki, N.; Knudsen, K. R.; Gothelf, K. V.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2001, 40, 2992-2995. Nitro aldol reactions: (c) Trost, B. M.; Yeh, V. S. C. Angew Chem., Int. Ed. 2002, 41, 861-863. (d) Shibasaki, M.; Sasai, H.; Arai, T. Angew Chem., Int. Ed. Engl. 1997, 36, 1236-1256. Thiol conjugate additions: (e) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417-430.
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21. 3tris(R-binaphthoxide) catalysis: (m) Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557-7558.
22. 3tris(R-binaphthoxide) catalysis: (m) Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557-7558.
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27. The addition reaction in nitromethane/THF (1:1 vol/vol) in the presence of A and TMP (10 mol % each) is called "standard conditions" hereafter.
28. 2O can be completed in a few minutes at room temperature.
29. 2)O showed a little higher selectivity, but a lower activity (rt, 144 h, 2a: 36%, 86% ee).
30. 2.
31. See Supporting Information.
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39. D -31.1° (c 1.08, MeOH)).