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Catalysed Asymmetric Protonation of Simple Linear Keto‐Enolic Species − A Route to Chiral α‐Arylpropionic Acids
Author(s) -
Roy Olivier,
Riahi Abdelkhalek,
Hénin Françoise,
Muzart Jacques
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200212)2002:23<3986::aid-ejoc3986>3.0.co;2-l
Subject(s) - chemistry , protonation , cinchonine , decarboxylation , enantioselective synthesis , cinchonidine , stereochemistry , catalysis , acid catalysis , aryl , ketone , organic chemistry , medicinal chemistry , ion , alkyl
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‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)