A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
| Autor: | Davide Brenna, Maurizio Benaglia, Anthony J. Burke, Margherita Pirola, Laura Raimondi |
|---|---|
| Přispěvatelé: | Waldmann, Herbert |
| Rok vydání: | 2017 |
| Předmět: |
Tamsulosin
Flow Chemistry Double bond Clinical Biochemistry Pharmaceutical Science 010402 general chemistry 01 natural sciences Biochemistry Catalysis Drug Discovery Organic chemistry Lewis acids and bases Amines Molecular Biology chemistry.chemical_classification Active ingredient Sulfonamides 010405 organic chemistry Active Pharmaceutical ingredient Continuous reactor Organic Chemistry Stereoisomerism Flow chemistry 0104 chemical sciences Enantiopure drug chemistry Indans Molecular Medicine Stereoselectivity Imines Oxidation-Reduction |
| Zdroj: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) Agência para a Sociedade do Conhecimento (UMIC)-FCT-Sociedade da Informação instacron:RCAAP |
| ISSN: | 0968-0896 |
| DOI: | 10.1016/j.bmc.2017.01.023 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect