Synthesis of Quaternary -Amino Esters: A Remarkably Broad Substrate Scope in Aza-Friedel−Crafts Alkylation

13 April 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

aza-Friedel−Crafts Alkylation
Quaternary -Amino Esters
silver(I) salt counteranion
Broad Substrate Scope
Phase-Transfer catalysis

Supplementary materials

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Supporting Information-0410-2020
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