Enantioselective and catalytic method for α-crotylation of aldehydes with a kinetic self-refinement of stereochemistry

Malkov, A. V., Kabeshov, M. A., Barlog, M. and Kocovsky, P. (2009) Enantioselective and catalytic method for α-crotylation of aldehydes with a kinetic self-refinement of stereochemistry. Chemistry: A European Journal, 15(7), pp. 1570-1573. (doi:10.1002/chem.200802224)

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Publisher's URL: http://dx.doi.org/10.1002/chem.200802224

Abstract

Kinetic refinery: A practical, highly stereoselective, two-step catalytic protocol for the α-allylation of aldehydes, starting from crotyltrichlorosilanes, has been developed (see scheme). In each reaction step, one of the stereoisomers reacted faster than the other, which resulted in a kinetic stereochemical (E/Z) self-refinement of the system and led to the formation of virtually enantiomerically and geometrically pure linear homoallylic alcohols in high yield.

Item Type:Articles
Keywords:Acid, aldehydes, allyl-transfer reaction, allylation, aromatic-aldehydes, assymetric allylation, asymetric catalysis, chiral lewis-bases, homoallylic alcohols, n-oxide, organocatalysts, reagents, rearrangement, route, stereoselectivity.
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Malkov, Dr Andrei and Barlog, Mr Maciej and Kocovsky, Professor Pavel
Authors: Malkov, A. V., Kabeshov, M. A., Barlog, M., and Kocovsky, P.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Chemistry: A European Journal
Journal Abbr.:Chem. Eur J.
Publisher:Wiley-VCH Verlag
ISSN:0947-6539
ISSN (Online):1521-3765
Published Online:02 January 2009

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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