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Synlett 1995; 1995(6): 631-633
DOI: 10.1055/s-1995-5013
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Diastereo- and Enantioselective Synthesis of β-Substituted γ,δ-Unsaturated α-Hydroxy-Ketones via [2,3]-Wittig Rearrangement of α-Allyloxyketone-Hydrazones

Dieter Enders* , Dirk Backhaus
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany
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Publikationsdatum:
31. Dezember 2000 (online)

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Asymmetric [2,3]-Wittig rearrangement of chiral hydrazones 2 affords α-hydroxy ketones 4 with various substituents in high enantiomeric excess and syn-diastereoselectivities, starting from readily available Weinreb-amides 1 in good overall yield.

α-hydroxy ketones - asymmetric synthesis - [2,3]-Wittig Rearrangement - Weinreb-amide - Grignard addition