224578-05-6Relevant articles and documents
Asymmetric biomimetic oxidations of phenols: The mechanism of the diastereo- and enantioselective synthesis of dehydrodiconiferyl ferulate (DDF) and dehydrodiconiferyl alcohol (DDA)
Orlandi, Marco,Rindone, Bruno,Molteni, Giorgio,Rummakko, Petteri,Brunow, G?sta
, p. 371 - 378 (2007/10/03)
Stereoselective bimolecular radical coupling of enantiopure phenylpropenoidic phenols are described, starting from enantiopure amidic derivatives of ferulic acid. The latter were prepared from ferulic acid by reaction with (S)-alanine or Oppolzer camphor sultam. The oxidation step was performed both enzymatically (HRP/H2O2) and chemically (Ag2O). The observed enantioselectivity in the oxidation step encompasses the range 65-84% and is consistent with the conformational analysis of the quinone methide intermediates at the PM3 level.