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Synlett 1991; 1991(11): 807-808
DOI: 10.1055/s-1991-20884
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Asymmetric Synthesis of (S)-2-Chloroalkanoic Acids with High Enantiomeric Excess by Diastereoselective Halogenation of α-D-Glucofuranose-Derived Silyl Ketene Acetals

L. Duhamel* , P. Angibaud, J. R. Desmurs, J. Y. Valnot
  • *URA CNRS 464, Faculté des Sciences et Techniques de Rouen, BP 118, F-76134 Mont Saint Aignan Cedex, France
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Publication Date:
07 March 2002 (online)

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Chlorination with N-chlorosuccinimide of silyl ketene acetals 2 prepared from chiral esters 1 (1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 3-alkanoates) and subsequent saponification of 2-chloro esters 3 provides (S)-2-chloroalkanoic acids with 75-90% enantiomeric excess and 65-72% overall yield from esters 1.