Cu(OTf)2 catalyzed trimethylsilyl cyanide addition to carbonyl compounds

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3823-3824

  Saravanan, P ^a   Anand, R Vijaya ^a   Singh, Vinod K ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBONYL DERIVATIVE; COPPER COMPLEX; COPPER ION; CYANIDE; KETONE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; HYDROLYSIS; SYNTHESIS;

EID: 0032575163     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00594-2     Document Type: Article

References (13)

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2. (b). Kaur, H.; Kaur, G.; Trehan, S. Synth. Commun. 1996, 26, 1925.
3. (c). Golinski, M.; Brock, C. P.; Watt, D. S. J. Org. Chem. 1993, 58, 159.
4. (d). Matsubara, S.; Takai, T.; Utimoto, K. Chem. Lett. 1991, 1447.
5. (e). Vougiouskas, A.E.; Kagan, H. B. Tetrahedron Lett. 1987, 28, 5513.
6. (f). Greenlee, W. J.; Hangauer, D. G. Tetrahedron Lett. 1983, 24, 4559.
7. (g). Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37, 3899.
8. (h). Gassman, P. G.; Talley, J. J. Org. Synth. 1981, 60, 14.
9. (i). Evans, D. A.; Truesdale, L. K.; Carroll, G. L. J. Chem. Soc., Chem. Commun. 1973, 55.
10. 2. Wang, D.; Yang, Y. Synlett 1997, 1379.
11. 3. For uncatalyzed reaction of TMSCN with aldehydes in MeCN, see: Manju, K.; Trehan, S. J. Chem. Soc., Perkin Trans. 1, 1995, 2383.
12. 4. Although we could also isolate TMS ether of cyanohydrin by quenching the reaction mixture with water, the isolated yield was low due to partial cleavage of silyl group to cyanohydrin. In fact, partial cleavage of TMS group was even observed during tlc run.
13. 2 it took 3h at rt.