Guangkuan Zhao1, Shyam S Samanta1, Jessica Michieletto1, Stéphane P Roche1,2. 1. Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, Florida 33431, United States. 2. Center for Molecular Biology and Biotechnology, Florida Atlantic University, Jupiter, Florida 33458, United States.
Abstract
A versatile synthetic protocol of aza-Friedel-Crafts alkylation has been developed for the synthesis of quaternary α-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, we also report a catalytic enantioselective example of the reaction.
A versatile synthetic protocol of aza-Friedel-Crafts alkylation has been developed for the synthesis of n class="Chemical">quaternary α-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, we also report a catalytic enantioselective example of the reaction.
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