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.
Enantioselective Allylation of α,β-Unsaturated Aldehydes with Allyltrichlorosilane Catalyzed by METHOX. -The title reaction provides a number of homoallylic alcohols with good to high enantioselectivity. -(MALKOV*, A. V.; BARLOG, M.; JEWKES, Y.; MIKUSEK, J.; KOCOVSKY, P.; J. Org. Chem. 76 (2011) 11, 4800-4804, http://dx.
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