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Synlett 1994; 1994(11): 969-971
DOI: 10.1055/s-1994-23068
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Enantioselective Synthesis of Allylic Alcohols via Asymmetric [2,3]-Sigmatropic Meisenheimer Rearrangement

Dieter Enders* , Hermann Kempen
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
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Publication Date:
22 March 2002 (online)

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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.