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Synlett 1992; 1992(11): 901-903
DOI: 10.1055/s-1992-21534
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Enantio- and Diastereoselective Synthesis of 3-Substituted Cyclic Hemiketals of ω-Hydroxy-2-oxoesters

Dieter Enders* , Hubert Dyker, Gerhard Raabe, Jan Runsink
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-5100 Aachen, Germany
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Publication Date:
08 March 2002 (online)

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The enantio- and diastereoselective synthesis of 3-substituted and unsubstituted cyclic hemiketals of ω-hydroxy-2-oxoesters as analogs of sialic and ulosonic acids is effectively achieved by a convenient four step sequence via alkylation of metalated N,N-dimethyl- and SAMP-hydrazones of 2-oxoesters with O-protected primary ω-hydroxy-alkyl iodides and subsequent cleavage of the hydrazone moiety and of the O-protecting group.

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