Enantio- and Diastereoselective Synthesis of 3-Substituted Cyclic Hemiketals of ω-Hydroxy-2-oxoesters

Dieter Enders; Hubert Dyker; Gerhard Raabe; Jan Runsink

doi:10.1055/s-1992-21534

Synlett 1992; 1992(11): 901-903
DOI: 10.1055/s-1992-21534

letter

© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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

Abstract

als PDF herunterladen Alle Artikel dieser Rubrik

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.

PDF (173 kb)