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Novel enantioselective synthesis of both enantiomers of furan-2-yl Amines and amino acids

Demir, Ayhan Sıtkı
Sesemoglu, O
Ulku, D
Arici, C
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.