Enantioselective Synthesis of Allylic AlcoholsviaAsymmetric [2,3]-Sigmatropic Meisenheimer Rearrangement

Abstract
Various allylic alcohols 6 are prepared in high enantiomeric excesses (ee = 93 - 99 %) by oxidation of readily available allylamines 3 bearing a C2-symmetrical amine moiety, followed by a [2,3]-sigmatropic Meisenheimer rearrangement of the resulting amine-N-oxide 4 and reductive N,O-bond cleavage of hydroxylamines 5.

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