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Synthesis 2005(17): 2962-2968
DOI: 10.1055/s-2005-872164
DOI: 10.1055/s-2005-872164
PAPER
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Synthesis of α- and α,β-Substituted β-Alkoxycarbonyl Sulfonates
Weitere Informationen
Received
17 May 2005
Publikationsdatum:
12. August 2005 (online)
Publikationsverlauf
Publikationsdatum:
12. August 2005 (online)
![](https://www.thieme-connect.de/media/synthesis/200517/lookinside/thumbnails/10.1055-s-2005-872164-1.jpg)
Abstract
An efficient asymmetric synthesis of substituted β-alkoxycarbonyl sulfonates is described. Enantiopure α-substituted β-alkoxycarbonyl sulfonates can be obtained via α-alkylation of metalated sulfonates bearing 1,2:5,6-di-O-isopropylidene-α-d-allofuranose as the chiral auxiliary with alkyl bromoacetates. α,β-Disubstituted β-alkoxycarbonyl sulfonates were prepared starting from the corresponding enantiopure γ-nitro sulfonates by using TFA for the cleavage of the chiral auxiliary and causing a simultaneous Meyer reaction.
Key words
asymmetric synthesis - sulfonates - esters - alkylation - sugar auxiliary
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