Catalysed Asymmetric Protonation of Simple Linear Keto??Enolic Species− A Route to Chiral α??Arylpropionic Acids

O Roy, A Riahi, F Hénin, J Muzart

Index: Roy, Olivier; Riahi, Abdelkhalek; Henin, Francoise; Muzart, Jacques European Journal of Organic Chemistry, 2002 , # 23 p. 3986 - 3994

Full Text: HTML

Citation Number: 15

Abstract

Abstract The reaction cascade consisting of deprotection/decarboxylation/asymmetric protonation of enolic species, starting from open-chain benzyl β-oxo esters, has been studied. When carried out in the presence of catalytic amounts of cinchonine, the reaction gave optically active α-aryl ketones with up to 75% ee. Enantio-enriched (S)-3-phenyl-2- butanone can be converted into 2-phenylpropionic acid without racemisation.(© Wiley- ...