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Synlett 1992; 1992(3): 239-240
DOI: 10.1055/s-1992-21327
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Tandem Dianionic Dioxy-Cope Rearrangement and Aldol Condensation: A Single-Pot Enantioselective Route to trans-4,5-Disubstituted 1-Cyclopentenecarbaldehyde from Acyclic Bisallylic Compounds

Seiki Saito* , Toshihide Yamamoto, Masanobu Matsuoka, Toshio Moriwake
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University, 3-1-1 Tsushima-naka, Okayama 700, Japan
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Publication Date:
08 March 2002 (online)

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The first example of dianionic dioxy-Cope rearrangement is presented. A dioxyanion prepared from a C 2 symmetric dienediol [(S,S)-1,8-bis(benzyloxy)-2,6-octadiene-4,5-diol (1)] with sodium bis(trimethylsilyl)amide undergoes a dioxy-Cope rearrangement to generate bis-enolate intermediate I 2, which, on protonation, followed by aldol reaction and base-promoted dehydration, gave (4R,5S)-4,5-bis(benzyloxymethyl)-1-cyclopentenecarbaldehyde [(-)-3] with complete chirality transmission from 1.