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submitted on 10.04.2020 and posted on 13.04.2020by Stephane Roche, Guangkuan zhao, Shyam Samanta, Jessica Michieletto
A versatile synthetic protocol of aza-Friedel−Crafts alkylation
has been developed for the synthesis of quaternary a-amino
esters. This operationally simple alkylation proceeds under ambient conditions
with high efficiency, regioselectivity, and an exceptionally broad scope of
arene nucleophiles. A key feature of this alkylation is the role associated
with the silver(I) salt counteranions liberated during the reaction. Taking
advantage of a phase-transfer counteranion/BrØnsted acid pair mechanism,
a catalytic enantioselective version of the reaction is also reported.