Enantioselective allylation of α,β-unsaturated aldehydes with allyltrichlorosilane catalyzed by METHOX

Andrei V Malkov; Maciej Barłóg; Yvonne Jewkes; Jirí Mikusek; Pavel Kocovský

doi:10.1021/jo200712p

Enantioselective allylation of α,β-unsaturated aldehydes with allyltrichlorosilane catalyzed by METHOX

J Org Chem. 2011 Jun 3;76(11):4800-4. doi: 10.1021/jo200712p. Epub 2011 May 12.

Authors

Andrei V Malkov¹, Maciej Barłóg, Yvonne Jewkes, Jirí Mikusek, Pavel Kocovský

Affiliation

¹ Department of Chemistry, WestChem, University of Glasgow, Glasgow, UK. a.malkov@lboro.ac.uk

PMID: 21534567
DOI: 10.1021/jo200712p

Abstract

α,β-Unsaturated aldehydes 6a-j undergo an enantioselective allylation with allylic trichlorosilanes 2a,b in the presence of METHOX (4) as a Lewis basic catalyst (≤10 mol %) to produce the homoallylic alcohols 7a-l at good to high enantioselectivity (83-96% ee). This study shows that the reactivity scope of METHOX can be extended from aromatic to nonaromatic aldehydes.