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
<b>Kinetic refinery:</b> 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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