Highly efficient silylcyanation of ketones by a catalytic double activation method using Lewis acid and N-oxide catalysts

Synlett

Volumn , Issue 4, 2003, Pages 558-560

  Chen, Fuxue ^b   Feng, Xiaoming ^a   Qin, Bo ^a   Zhang, Guolin ^c   Jiang, Yaozhong ^b  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

Cyanohydrins; Double activation catalysis; Ketones; N oxides; Schiff bases

Indexed keywords

CYANOHYDRIN; KETONE; LEWIS ACID; OXIDE; SCHIFF BASE; TITANIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; CYCLIZATION; METAL BINDING; REACTION ANALYSIS; SILYLATION;

EID: 0037240111     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37534     Document Type: Article

References (24)

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12. The ligand was prepared as described in: (a) Jiang, Y. Z.; Gong, L. Z.; Feng, X. M.; Hu, W. H.; Pan, W. D.; Li, Z.; Mi, A. Q. Tetrahedron 1997, 53, 14327. (b) For other examples of achiral salen-Mn/Cr complexes, see: Srinivasan, K.; Michaud, P.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309. (c) See also: Samel, E. G.; Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1985, 107, 7606.
13. The ligand was prepared as described in: (a) Jiang, Y. Z.; Gong, L. Z.; Feng, X. M.; Hu, W. H.; Pan, W. D.; Li, Z.; Mi, A. Q. Tetrahedron 1997, 53, 14327. (b) For other examples of achiral salen-Mn/Cr complexes, see: Srinivasan, K.; Michaud, P.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309. (c) See also: Samel, E. G.; Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1985, 107, 7606.
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16. Our related research on hydrocyanation of aldehydes, see: (a) Pan, W. D.; Feng, X. M.; Gong, L. Z.; Hu, W. H.; Li, Z.; Mi, A. Q.; Jiang, Y. Z. Synlett 1996, 337. (b) Feng, X. M.; Gong, L. Z.; Hu, W. H.; Li, Z.; Pan, W. D.; Mi, A. Q.; Jiang, Y. Z. Chem. J. Chin. Univ. 1998, 19, 1416. (c) On Strecker reaction, see: Liu, B.; Feng, X. M.; Chen, F. X.; Zhang, G. L.; Jiang, Y. Z. Synlett 2001, 1551.
17. Our related research on hydrocyanation of aldehydes, see: (a) Pan, W. D.; Feng, X. M.; Gong, L. Z.; Hu, W. H.; Li, Z.; Mi, A. Q.; Jiang, Y. Z. Synlett 1996, 337. (b) Feng, X. M.; Gong, L. Z.; Hu, W. H.; Li, Z.; Pan, W. D.; Mi, A. Q.; Jiang, Y. Z. Chem. J. Chin. Univ. 1998, 19, 1416. (c) On Strecker reaction, see: Liu, B.; Feng, X. M.; Chen, F. X.; Zhang, G. L.; Jiang, Y. Z. Synlett 2001, 1551.
18. When NMO (N-methylmorpholine N-oxide) and PyNO (pyridine N-oxide) were used as the Lewis bases under the optimized conditions, the yield was reduced to 42% and 52%, respectively.
19. 2 (1.0 mL), which was also stirred at 35°C for 1 h. The reaction was performed at 23°C. At completion, the reaction mixture was concentrated and put on a silica gel column to give the O-TMS cyanohydrin as clear colorless oil (680 mg, 97%).
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24. r(minor) = 25.4 min}.