Tetrabutylammonium cyanide catalyzes the addition of TMSCN to aldehydes and ketones

Arkivoc

Volumn 2004, Issue 4, 2004, Pages 94-99

  Córdoba, Rubén ^a   Csákÿ, Aurelio G ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Ammonium salts; Catalysis; Cyanohydrins; Trimethylsilyl cyanide

Indexed keywords

2 TRIMETHYLSILANYLOXY 6 OXABICYCLO[3.1.0]HEXANE 2 CARBONITRILE; 2 TRIMETHYLSILANYLOXY 7 OXABICYCLO[4.1.0]HEPTANE 2 CARBONITRILE; 2,4 DIBROMO 3,5 DIMETHOXYCYCLOHEXA 2,4 DIENE 1 ONE 5 SPIROOXIRANE; 5,7 DIBROMO 6,8 DIMETHOXY 4 TRIMETHYLSILANYLOXY 1 OXASPIRO[2.5]OCTA 5,7 DIENE 4 CARBONITRILE; 6 METHOXY 4 TRIMETHYLSILANYLOXY 1 OXASPIRO[2.5]OCTA 5,7 DIENE 4 CARBONITRILE; 7 BROMO 4 TRIMETHYLSILANYLOXY 1 OXASPIRO[2.5]OCTA 5,7 DIENE 4 CARBONITRILE; ALDEHYDE; ANISALDEHYDE; BENZALDEHYDE; CARBONYL DERIVATIVE; CYANIDE; CYANOHYDRIN; CYCLOHEXANONE; CYCLOPENTANE DERIVATIVE; CYCLOPENTANONE; FURFURAL; KETONE; SPIROEPOXYCYCLOHEXADIENONE DERIVATIVE; TETRABUTYLAMMONIUM CYANIDE; TRIMETHYLSILYL CYANIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 2942670706     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (14)

1. For a recent review, see: Gregory, R. J. H. Chem. Rev. 1999, 99, 3649
2. See ref. 1 and: (a) Saravan, P.; Anand, R. V.; Singh, V. K. Tetrahedron Lett. 1998, 39, 3823.
3. (b) Somathan, R.; Rivero, I. A.; Gama, A.; Ochoa, A.; Aguirre, G. Synth. Commun. 1998, 28, 2043.
4. (c) Kantam, M. L.; Sreekanth, P.; Santhi, P. L. Green Chem. 2000, 2, 47.
5. (d) Wang, Z. G.; Fetterly, B.; Verkade, J. G. J. J. Organomet. Chem. 2002, 646, 161.
6. (e) Yadav, J. S.; Reddy, M. S.; Prasad, A. R. Tetrahedron Lett. 2002, 43, 9703.
7. (f) Bandini, M.; Cozzi, P. G.; Garelli, A.; Melchiorre, P.; Umani-Ronchi, A. Eur. J. Org. Chem. 2002, 3243.
8. (g) Córdoba, R.; Plumet, J. Tetrahedron Lett. 2003,44, 6157.
9. Spiroepoxycyclohexadienones are useful synthetic intermediates mainly in the context of their reactivity as dienes in Diels-Alder reactions. For some selected accounts, see: (a) Singh, V. Acc. Chem. Res. 1999, 32, 324.
10. (b) Bonnarme, V.; Bachmann, Ch.; Cousson, A.; Mondon, M.; Gesson, J. P. Tetrahedron 1999, 55, 433.
11. (c) Bonnarme, V.; Mondon, M.; Cousson, A.; Gesson, J. P. Chem. Comm. 1999, 1143.
12. (d) Quideau, S.; Poységu, L. Org. Prep. Proc. Int. 1999, 31, 617.
13. Hinterding, K.; Knebel, A.; Herrlich, P.; Waldmann, H. Bioorg. Med. Chem. 1998, 6, 1153.
14. Evans, D. A.; Truesdale, L. K. Tetrahedron Lett.1973,14, 4929.