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Waste Minimized Multistep Preparation in Flow of β-Amino Acids Starting from α,β-Unsaturated Carboxylic Acids
- Eleonora Ballerini
- ,
- Massimo Curini
- ,
- Dmitri Gelman
- ,
- Daniela Lanari
- ,
- Oriana Piermatti
- ,
- Ferdinando Pizzo
- ,
- Stefano Santoro
- , and
- Luigi Vaccaro
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† Laboratory of Green Synthetic Organic Chemistry, CEMIN - Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto, 8, 06123 Perugia, Italia
‡ Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo, 06123 Perugia, Italia
§ Institute of Chemistry, The Hebrew University, Edmond Safra Campus, Givat Ram, 91904 Jerusalem, Israel
*Luigi Vaccaro. Fax: +39 075 5855560. Tel: +39 075 5855541. E-mail: [email protected]
Abstract
An efficient protocol for the synthesis of β-amino acids starting from easily accessible α,β-unsaturated carboxylic acids based on the combination of two heterogeneous catalytic systems is reported. This multistep approach is based on the direct β-azidation of α,β-unsaturated carboxylic acids and subsequent azido group reduction performed in flow conditions. It has been demonstrated that the catalysts can be easily recovered and reused conserving its complete efficiency. The green metrics calculations proved the high environmental efficiency of the protocol characterized by very low waste production.
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