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Novel Enantioselective Synthesis of Both Enantiomers of Furan‐2‐yl Amines and Amino Acids
Author(s) -
Demir Ayhan S.,
Sesenoglu Özge,
Ülkü Dinçer,
Arıcı Cengiz
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390022
Subject(s) - enantioselective synthesis , chemistry , furan , oxime , enantiomer , ketone , ring (chemistry) , amino acid , organic chemistry , stereochemistry , catalysis , biochemistry
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.