Preparation and Reactions of 2,2-Dimethyl-1,3-dioxan-5-one-SAMP-Hydrazone: A Versatile Chiral Dihydroxyacetone Equivalent

Preparation and Reactions of 2,2-Dimethyl-1,3-dioxan-5-one-SAMP-Hydrazone: A Versatile Chiral Dihydroxyacetone Equivalent

Abstract The SAMP-hydrazone of 2,2-dimethyl-1,3-dioxan-5-one represents a valuable chiral dihydroxyacetone equivalent. Asymmetric mono- or α,α′-bisalkylations followed by auxiliary cleavage leads to the corresponding mono- or α,α′-disubstituted, acetonide protected ketodiols in excellent diastereo-...

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Veröffentlicht in:Synthesis (Stuttgart) 2002, Vol.2002 (12), p.1775-1779
Hauptverfasser: Enders, Dieter, Voith, Matthias, Ince, Stuart J.
Format: Artikel
Sprache:eng
Schlagworte:
practical synthetic procedures
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Zusammenfassung:Abstract The SAMP-hydrazone of 2,2-dimethyl-1,3-dioxan-5-one represents a valuable chiral dihydroxyacetone equivalent. Asymmetric mono- or α,α′-bisalkylations followed by auxiliary cleavage leads to the corresponding mono- or α,α′-disubstituted, acetonide protected ketodiols in excellent diastereo- and enantiomeric excesses.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2002-33646