In the field of APIs (Active Pharmaceutical Ingredients), the industry is gradually progressing towards enantiopure formulations. In this context, chiral amines are unanimously considered a class of paramount importance, due to their widespread diffusion in a plethora of compounds. In the present study it is reported a catalytic, metal-free approach to the synthesis of chiral amines, direct precursors of two important APIs: Letermovir (a), a drug that shows great promise for the next-generation treatment of HCMV (human Cytomegalovirus) infection; fluorinated Retro-thiorphan peptide mimetic (b), a potent and selective inhibitor of the metalloproteinase NEP (neutral endopeptidase). The key step in both synthesis is the stereoselective catalytic reduction of an enamine moiety; we decided to perform this transformation using a metal-free reducing agent, trichlorosilane (HSiCl3), in combination with a catalytic amount of a chiral Lewis base (LB) as organocatalyst.

Stereoselective catalytic synthetic strategies for active pharmaceutical ingredients (API) precursors / M. Pirola, M. Benaglia. ((Intervento presentato al convegno EFCATS School on Catalysis tenutosi a Liblice Castle nel 2018.

Stereoselective catalytic synthetic strategies for active pharmaceutical ingredients (API) precursors

M. Pirola;M. Benaglia
2018-06

Abstract

In the field of APIs (Active Pharmaceutical Ingredients), the industry is gradually progressing towards enantiopure formulations. In this context, chiral amines are unanimously considered a class of paramount importance, due to their widespread diffusion in a plethora of compounds. In the present study it is reported a catalytic, metal-free approach to the synthesis of chiral amines, direct precursors of two important APIs: Letermovir (a), a drug that shows great promise for the next-generation treatment of HCMV (human Cytomegalovirus) infection; fluorinated Retro-thiorphan peptide mimetic (b), a potent and selective inhibitor of the metalloproteinase NEP (neutral endopeptidase). The key step in both synthesis is the stereoselective catalytic reduction of an enamine moiety; we decided to perform this transformation using a metal-free reducing agent, trichlorosilane (HSiCl3), in combination with a catalytic amount of a chiral Lewis base (LB) as organocatalyst.
Settore CHIM/06 - Chimica Organica
Stereoselective catalytic synthetic strategies for active pharmaceutical ingredients (API) precursors / M. Pirola, M. Benaglia. ((Intervento presentato al convegno EFCATS School on Catalysis tenutosi a Liblice Castle nel 2018.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/630663
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