83657-23-2Relevant academic research and scientific papers
Highly stereoselective Friedel-Crafts type cyclization. Facile access to enantiopure 1,4-dihydro-4-phenyl isoquinolinones
Philippe, Nicolas,Denivet, Fran?ois,Vasse, Jean-Luc,Sopkova-De Olivera Santos, Jana,Levacher, Vincent,Dupas, Georges
, p. 8049 - 8056 (2007/10/03)
The present report describes a stereoselective synthesis of 1,4-dihydro-4-phenyl isoquinolinones 5 based on a stereoselective Friedel-Crafts type cyclization. Cyclization precursors 1 were prepared in two steps, from the readily available (S)-mandelic acid, in 60-80% overall yield. The stereoselective electrophilic cyclization was accomplished in 20-86% yield and with 20-97% ee. In the course of this work, the presence of the amide carbonyl was found to be particularly important to guarantee a stereospecific process during the electrophilic aromatic substitution.
EFFICIENT ASYMMETRIC HYDROGENATION OF α-AMINOACETOPHENONE DERIVATIVES LEADING TO PRACTICAL SYNTHESIS OF (S)-(-)-LEVAMISOLE
Takeda, Hideo,Tachinami, Takeshi,Aburatani, Masakazu,Takahashi, Hisashi,Morimoto, Toshiaki,Achiwa, Kazuo
, p. 363 - 366 (2007/10/02)
The neutral (2S,4S)-MCCPM-rhodium complex was found to be an efficient catalyst for asymmetric hydrogenation of α-aminoacetophenone derivatives.A practical asymmetric synthesis of (S)-(-)-levamisole was realized by using this hydrogenation as a key reaction.
