Synthesis 2002(12): 1775-1779
DOI: 10.1055/s-2002-33646
PSP
© Georg Thieme Verlag Stuttgart · New York

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

Dieter Enders*, Matthias Voith, Stuart J. Ince
Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: [email protected];
Further Information

Publication History

Received 5 April 2002
Publication Date:
05 September 2002 (online)

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.

    References

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15

Enders, D.; Voith, M., unpublished results.