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Synthesis 1996; 1996(12): 1438-1442
DOI: 10.1055/s-1996-4412
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Diastereo- and Enantioselective Synthesis of Polyfunctional Cyclic Ketones with Neighboring Quaternary and Tertiary Stereogenic Centers via [2,3]-Wittig Rearrangement

Dieter Enders* , Michael Bartsch, Dirk Backhaus, Jan Runsink, Gerhard Raabe
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany, Fax +49(241)8888127; E-mail: Enders@RWTH-Aachen.de
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Publication Date:
31 December 2000 (online)

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The diastereo- and enantioselective synthesis of β-substituted γ,δ-unsaturated cyclic α-hydroxy ketones 4 with neighboring quarternary and tertiary stereogenic centers via asymmetric [2,3]-Wittig rearrangement of SAEP-hydrazones 2 with good overall yields (58-74%), high anti-selectivities (92-94%) and excellent enantiomeric excesses (ee ≥ 96%) is described. The absolute configuration is determined by X-ray structure analysis of the hydrazone 3b and by 1H NMR NOE measurements.

[2,3]-Wittig rearrangement - polyfunctional ketones - chiral hydrazone - asymmetric synthesis - quarternary stereogenic center

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