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

✍ Scribed by Ayhan S. Demir; Özge Sesenoglu; Dinçer Ülkü; Cengiz Arıcı

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 245 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390022

✦ Synopsis

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 acids in high yields.