144075-97-8Relevant academic research and scientific papers
Towards a universal organocatalyst for the synthesis of enantioenriched phenylalanine derivatives by enantioselective decarboxylative protonation
Pigeaux, Morgane,Laporte, Romain,Harrowven, David C.,Baudoux, Jér?me,Rouden, Jacques
, p. 4599 - 4603 (2016)
Access to enantioenriched non-proteogenic phenylalanine derivatives is described using the enantioselective decarboxylative protonation reaction of amidohemimalonate esters catalysed by various cinchona-based compounds. This study compares the catalytic efficiency as well as the enantioselectivity induced by three types of common organocatalysts, namely thioureas, squaramides and bis-cinchona squaramides. One of the main outcome of this work is the observation of a significant influence of the N-protecting group of the hemimalonate on its interaction with the catalyst. This methodology carried out under mild conditions exhibits good substrate scope and functional group tolerance. A substoichiometric amount of catalyst can also be used in certain cases while affording good yields and selectivities.
