The diastereoselective, trichlorosilane-mediate reduction of imines, bearing different and removable chiral auxiliaries, in combination either with achiral bases or catalytic amounts of chiral Lewis bases, was investigated to afford immediate precursors of chiral APIs (Active Pharmaceutical Ingredients). The carbon-nitrogen double bond reduction was successfully performed in batch and in flow mode, in high yields and almost complete stereocontrol. By this metal-free approach, the formal synthesis of rasagiline and tamsulosin was successfully accomplished in micro(meso) flow reactors, under continuous flow conditions. The results of these explorative studies represent a new, important step towards the development of automated processes for the preparation of enantiopure biologically active compounds.
|Titolo:||Stereoselective synthesis of pharmaceutically active Chiral amnes|
|Data di pubblicazione:||27-nov-2017|
|Parole Chiave:||Chiral amines; stereoselective synthesis; trichlorosilane|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Citazione:||Stereoselective synthesis of pharmaceutically active Chiral amnes / M. Pirola, F. Cozzi, M. Benaglia. ((Intervento presentato al convegno Nuovi Orientamenti nella Sintesi Organica tenutosi a Milano nel 2017.|
|Appare nelle tipologie:||14 - Intervento a convegno non pubblicato|