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Synthesis 1996; 1996(9): 1095-1100
DOI: 10.1055/s-1996-4341
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Highly Diastereoselective Boron-Mediated anti-Aldol Reactions of 4-Silyl Substituted 2,2-Dimethyl-1,3-dioxan-5-one. Diastereo- and Enantioselective Synthesis of Protected Oxopolyols

Dieter Enders* , Oleg F. Prokopenko, Gerhard Raabe, Jan Runsink
  • *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 boron enolate of 4-silylated 2,2-dimethyl-1,3-dioxan-5-one (S)-3 reacts with representative aldehydes in a highly anti diastereoselective aldol reaction to give the corresponding adducts (S,S,S)-4 in 78-93% yield with diastereoisomeric excesses of de = 96-98%. The removal of the silyl group via the triethylamine-trihydrofluoride complex leads to protected oxopolyols (S,S)-5 in good yields (64-79%) with excellent diastereomeric and enantiomeric excesses (de,ee = 96-98%). The absolute configuration was determined by X-ray structure analysis of (S,S)-5c.

asymmetric synthesis - α-silyl ketones - aldol reaction - SAMP-hydrazones - protected oxopolyols