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.
|Titolo:||A continuous flow, two-steps, metal-free process for the synthesis of differently substituted chiral 1,2-diamino derivatives|
|Parole Chiave:||flow chemistry; chiral diamines; microreactors; nitroenamines; organocatalysis|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2018|
|Digital Object Identifier (DOI):||10.1055/s-0036-1591911|
|Appare nelle tipologie:||01 - Articolo su periodico|