The enantioselective organocatalytic reduction of aryl-substituted nitroenamines was successfully performed under continuous-flow conditions. After a preliminary screening with a 10-L microreactor, to establish the best reaction conditions, the reduction was scaled up in a 0.5-mL mesoreactor, without appreciable loss of enantioselectivity, that remained constantly higher than 90%. The in-flow nitro reduction was also accomplished, either by Raney nickel catalyzed hydrogenation or by a metal-free methodology based on the use of the very inexpensive and readily available reducing agent trichlorosilane. The final aim is to develop a two-step, continuous-flow process for the stereoselective, metal-free, catalytic synthesis of differently functionalized chiral 1,2-diamines.

A continuous flow, two-steps, metal-free process for the synthesis of differently substituted chiral 1,2-diamino derivatives / M. Pirola, M. Benaglia, M.E. Compostella, L. Raimondi, A. Puglisi. - In: SYNTHESIS. - ISSN 0039-7881. - 50:7(2018), pp. 1430-1438. [10.1055/s-0036-1591911]

A continuous flow, two-steps, metal-free process for the synthesis of differently substituted chiral 1,2-diamino derivatives

PIROLA, MARGHERITA;M. Benaglia;COMPOSTELLA, MARIA ELENA;L. Raimondi;A. Puglisi
2018

Abstract

The enantioselective organocatalytic reduction of aryl-substituted nitroenamines was successfully performed under continuous-flow conditions. After a preliminary screening with a 10-L microreactor, to establish the best reaction conditions, the reduction was scaled up in a 0.5-mL mesoreactor, without appreciable loss of enantioselectivity, that remained constantly higher than 90%. The in-flow nitro reduction was also accomplished, either by Raney nickel catalyzed hydrogenation or by a metal-free methodology based on the use of the very inexpensive and readily available reducing agent trichlorosilane. The final aim is to develop a two-step, continuous-flow process for the stereoselective, metal-free, catalytic synthesis of differently functionalized chiral 1,2-diamines.
flow chemistry; chiral diamines; microreactors; nitroenamines; organocatalysis
Settore CHIM/06 - Chimica Organica
SYNTHESIS
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/554457
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