Synthesis of γ-functionalized allyltrichlorosilanes and their application in the asymmetric allylation of aldehydes

Malkov, A. V., MacDonald, C. and Kočovský, P. (2010) Synthesis of γ-functionalized allyltrichlorosilanes and their application in the asymmetric allylation of aldehydes. Tetrahedron: Asymmetry, 21(9-10), pp. 1173-1175. (doi:10.1016/j.tetasy.2010.03.026)

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Publisher's URL: http://dx.doi.org/10.1016/j.tetasy.2010.03.026

Abstract

Isomerically pure trans- and cis-γ-bromoallyltrichlorosilanes 4 and 5 have been synthesized and shown to react with aromatic aldehydes 1 in the presence of Lewis-basic catalysts (e.g., DMF) to produce the corresponding anti- and syn-allylbromohydrins 8 and 9, respectively, as single diastereoisomers. With BINAPO 25 as a chiral catalyst, promising enantioselectivity (⩽50% ee) has been attained.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Malkov, Dr Andrei and MacDonald, Miss Claire and Kocovsky, Professor Pavel
Authors: Malkov, A. V., MacDonald, C., and Kočovský, P.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron: Asymmetry
Publisher:Elsevier
ISSN:0957-4166
ISSN (Online):1362-511X
Published Online:03 May 2010

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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