Novel Enantioselective Synthesis of Both Enantiomers of Furan??2??yl Amines and Amino Acids

AS Demir, O Sesenoglu, D Uelkue…

Index: Demir, Ayhan S.; Sesenoglu, Oezge; Uelkue, Dincer; Arici, Cengiz Helvetica Chimica Acta, 2003 , vol. 86, # 1 p. 91 - 105

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Citation Number: 40

Abstract

Abstract 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 ...