New pyridine N-oxides as chiral organocatalysts in the asymmetric allylation of aromatic aldehydes

Malkov, A. V., Westwater, M. M., Gutnov, A., Ramirez-Lopez, P., Friscourt, F., Kadlcikova, A., Hodacova, J., Rankovic, Z., Kotora, M. and Kocovsky, P. (2008) New pyridine N-oxides as chiral organocatalysts in the asymmetric allylation of aromatic aldehydes. Tetrahedron, 64(49), pp. 11335-11348. (doi:10.1016/j.tet.2008.08.084)

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Abstract

Asymmetric allylation of aromatic aldehydes 1 with allyltrichlorosilane (2) can be catalyzed by new terpene-derived bipyridine N,N'-dioxides 12-15 and an axially chiral biisoquinoline dioxide 17b with good enantioselectivities. Dioxides have been found to be more reactive catalysts than their monooxide counterparts. Crown Copyright . All rights reserved.

Item Type:Articles
Keywords:ALDEHYDES allylation ALLYLIC OXIDATION Allylsilane ALLYLTRICHLOROSILANE ALLYLTRICHLOROSILANES AROMATIC-ALDEHYDES ASYMMETRIC ALLYLATION Asymmetric catalysis ATROPOISOMERIC BIPYRIDINE N,N'-DIOXIDES CARBONYL-COMPOUNDS CATALYST CATALYSTS Chiral CYCLOPROPANATION EFFICIENT CATALYST ENANTIOSELECTIVE ALLYLATION ISOQUINOLINES LIGANDS N-OXIDE Organocatalysis ORGANOCATALYSTS Pyridine Pyridine N-oxides TERMINAL ACETYLENES
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Malkov, Dr Andrei and Kocovsky, Professor Pavel
Authors: Malkov, A. V., Westwater, M. M., Gutnov, A., Ramirez-Lopez, P., Friscourt, F., Kadlcikova, A., Hodacova, J., Rankovic, Z., Kotora, M., and Kocovsky, P.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron
ISSN:0040-4020

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
384741Organocatalysts in asymmetric reactions mediated by silicon reagentsPavel KocovskyEngineering & Physical Sciences Research Council (EPSRC)GR/T27051/01Chemistry