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Organocatalytic Enantioselective Decarboxylative Protonation Reaction of Meldrum's Acid Derivatives under PTC Conditions
Author(s) -
Legros Fabien,
Martzel Thomas,
Brière JeanFrançois,
Oudeyer Sylvain,
Levacher Vincent
Publication year - 2018
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/ejoc.201800331
Subject(s) - chemistry , enantioselective synthesis , protonation , organocatalysis , meldrum's acid , organic chemistry , catalysis , decarboxylation , propionates , ammonium , phenols , aryl , combinatorial chemistry , ion , alkyl
An original organocatalyzed enantioselective protonation sequence of a transient quaternary ammonium enolate species has been developed by starting from readily available disubstituted Meldrum's acid derivatives and phenols. Under phase‐transfer‐catalytic (PTC) conditions, chiral nonracemic 2‐aryl propionic ester derivatives were obtained in good isolated yields with enantioselectivities up to 70 % ee . The usefulness of the approach was demonstrated by the synthesis of enantioenriched ( S )‐ibuprofen.