Asymmetric Synthesis of 2-Chloro- and 2-Bromo-alkanoic acids by Halogenation of α-D-Glucofuranose-Derived Silyl Ketene Acetals.
Optically active (S)-2-bromo- and 2-chloro-alkanoic acids 6 and 7 have been obtained via the diastereoselective halogenation of chiral silyl ketene acetals 3a-f, and subsequent saponification of the resulting crude esters.Examples characterized by e.e. values up to 95percent are reported.The diastereoface selectivity is independent of the silyl ketene acetal E/Z configuration.
Angibaud, P.,Chaumette, J. L.,Desmurs, J. R.,Duhamel, L.,Ple, G.,et al.
p. 1919 - 1932
(2007/10/03)
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