Copper(II) trifluoromethanesulfonate catalyzed addition of a carbamoylsilane to aldehyde imines

Synlett

Volumn , Issue 20, 2005, Pages 3157-3159

  Cunico, Robert F ^a   Pandey, Rajesh K ^a   Chen, Jianxin ^a   Motta, Adalie R ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

Aminoamides; Carbamoylsilane; Carbenes; Copper trifluoromethanesulfonate; Imine addition

Indexed keywords

ALDEHYDE DERIVATIVE; ALDEHYDE IMINE; CARBAMIC ACID DERIVATIVE; CARBAMOYLSILANE; CARBENOID; COPPER DERIVATIVE; COPPER TRIFLUOROMETHANESULFONATE; N,N DIMETHYL ALPHA (N METHYLAMINO)AMIDE; N,N DIMETHYLCARBAMOYL (TRIMETHYL)SILANE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 29744467733     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-922749     Document Type: Article

References (11)

1. Katritzky, A. R.; Kirichenko, N.; Rogovoy, B. V.; He, H.-Y. J. Org. Chem. 2003, 68, 9088; and references therein.
2. Review: Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
3. For current examples, see: (a) Pick, R.; Bauer, M.; Kazmaier, U.; Hebach, C. Synlett 2005, 757.
4. (b) Basso, A.; Banfi, L.; Riva, R.; Guanti, G. J. Org. Chem. 2004, 70, 575.
5. Chen, J.; Cunico, R. F. Tetrahedron Lett. 2003, 44, 8025.
6. Chen, J.; Pandey, R. K.; Cunico, R. F. Tetrahedron: Asymmetry 2005, 16, 941.
7. 3); C, H, N combustion analysis].
8. (a) Evidence for this possibility with organopalladium(II) halides has been presented: Cunico, R. F.; Maity, B. C. Org. Lett. 2003, 5, 4947.
9. (b) Additional mechanistic discussions can be found in: Cunico, R. F.; Motta, A. R. Org. Lett. 2005, 7, 771.
10. There is no reaction between 1 and N-methylbenzaldehyde imine at 100 °C.
11. Strongly polarized iminium salts have been shown to easily add 1, even if the imine carbon atom is highly hindered: Chen, J.; Cunico, R. F. Tetrahedron Lett. 2002, 43, 8595; characterization data for 5 are reported in this work.