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Synlett 1999; 1999(9): 1447-1449
DOI: 10.1055/s-1999-2862
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Stereoselective Synthesis of Protected Ketohexoses via Aldol Reaction of Chiral Dioxanone Enolate

Marek Majewski* , Pawel Nowak
  • *Department of Chemistry, University of Saskatchewan, 110 Science Pl., Saskatoon, SK, S7N 5C9, Canada
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Publication Date:
31 December 1999 (online)

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Lithium and boron enolates of 2,2-dialkyl-1,3-dioxa-5-ones react with aldehydes to give aldol products in high diastereoselectivity and, when chiral lithium enolates are generated using optically pure chiral lithium amide bases, in high enantioselectivity. Dioxanone lithium enolates react readily with protected glyceraldehyde affording protected ketohexoses in high diastereo- and enantiomeric purity.

dioxanone - enantioselective deprotonation - chiral lithium amides