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 Kocovsky, Professor Pavel and MacDonald, Dr Claire |
| Authors: | Malkov, A. V., MacDonald, C., and Kočovský, P. |
| College/School: | College of Science and Engineering > School of Chemistry College of Medical Veterinary and Life Sciences > School of Infection & Immunity > Centre for Virus Research |
| Journal Name: | Tetrahedron: Asymmetry |
| Publisher: | Elsevier |
| ISSN: | 0957-4166 |
| ISSN (Online): | 1362-511X |
| Published Online: | 03 May 2010 |
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