Journal
HELVETICA CHIMICA ACTA
Volume 86, Issue 1, Pages 91-105Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.200390022
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A new enantioselective synthesis of furan-2-yl amines and amino acids is described, in which the key step is the oxazaborolidine-catalyzed enantioselective reduction of O-benzyl (E)- and (Z)-furan-2-yl ketone oximes to the corresponding chiral amines. The chirality of the furan-2-yl amines is fully controlled by the appropriate choice of the geometrical isomer of the O-benzyl oxime. Oxidation of the furan ring furnished amino acids in high yields.
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