Abstract
Allylation of aldehydes by an allyl-transfer reaction from the γ-adducts of homoallylic alcohols has been successfully carried out to give the corresponding α-adducts regioselectively. This unusual allylation reaction appears to proceed stereoselectively through a 2-oxonium [3.3] -sigmatropic rearrangement with six-membered cyclic chair-like transition state. We applied this for asymmetric alk-2-enylation of aldehydes by chiral alk-2-enyl donors prepared from cheap and readily available optically pure ketones such as (-) - or (+) -menthone.
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