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A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin.
Brenna, Davide; Pirola, Margherita; Raimondi, Laura; Burke, Anthony J; Benaglia, Maurizio.
Afiliación
  • Brenna D; Dipartimento di Chimica, Universita' degli Studi di Milano, via Golgi 19, 20133 Milano, Italy.
  • Pirola M; Dipartimento di Chimica, Universita' degli Studi di Milano, via Golgi 19, 20133 Milano, Italy.
  • Raimondi L; Dipartimento di Chimica, Universita' degli Studi di Milano, via Golgi 19, 20133 Milano, Italy.
  • Burke AJ; Department of Chemistry and Chemistry Center of Évora, University of Évora, Rua Romão Ramalho, 59, 7000 Évora, Portugal.
  • Benaglia M; Dipartimento di Chimica, Universita' degli Studi di Milano, via Golgi 19, 20133 Milano, Italy. Electronic address: maurizio.benaglia@unimi.it.
Bioorg Med Chem ; 25(23): 6242-6247, 2017 12 01.
Article en En | MEDLINE | ID: mdl-28153587
ABSTRACT
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.
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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Sulfonamidas / Indanos Idioma: En Revista: Bioorg Med Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2017 Tipo del documento: Article País de afiliación: Italia

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Sulfonamidas / Indanos Idioma: En Revista: Bioorg Med Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2017 Tipo del documento: Article País de afiliación: Italia