Malkov, A. V., Stoncius, S., MacDougall, K. N., Mariani, A., McGeoch, G. D. and Kocovsky, P. (2006) Formamides derived from N-methyl amino acids serve as new chiral organocatalysts in the enantioselective reduction of aromatic ketimines with trichlorosilane. Tetrahedron, 62(2-3), pp. 264-284. (doi: 10.1016/j.tet.2005.08.117)
Full text not currently available from Enlighten.
Publisher's URL: http://dx.doi.org/10.1016/j.tet.2005.08.117
Abstract
Asymmetric reduction of N-aryl ketimines 1a–k, 43, and 45 with trichlorosilane can be catalyzed by new N-methyl l-amino acid-derived Lewis-basic organocatalysts, such as the valine-derived bisamide 3d (10 mol%), in toluene at room temperature with high enantioselectivity (≤92% ee). The structure–reactivity investigation shows that the product configuration is controlled by the nature of the side chain of the catalyst scaffold (e.g., i-Pr vs Me, as in 3d and 6e), so that catalysts of the same absolute configuration may induce the formation of the opposite enantiomers of the product. Arene–arene interactions between the catalyst and the incoming imine appear to be the prerequisite for asymmetric induction. This metal-free, organocatalytic protocol is competitive with the traditional, metal-catalyzed methodology.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Stoncius, Mr Sigitas and Kocovsky, Professor Pavel and McGeoch, Mr Grant |
| Authors: | Malkov, A. V., Stoncius, S., MacDougall, K. N., Mariani, A., McGeoch, G. D., and Kocovsky, P. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Tetrahedron |
| Publisher: | Elsevier |
| ISSN: | 0040-4020 |
| ISSN (Online): | 1464-5416 |
| Published Online: | 10 October 2005 |
University Staff: Request a correction | Enlighten Editors: Update this record
Altmetric
Altmetric