ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
0/0

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

preprint
submitted on 10.04.2020 and posted on 13.04.2020 by 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.

Funding

Asymmetric Synthesis of Unnatural ?-Amino Acids: Applications to Natural Products

National Institute of General Medical Sciences

Find out more...

Flexible Rigidity in Peptide Drug Design for Protein-Protein Interaction Inhibitors

National Institute of General Medical Sciences

Find out more...

History

Email Address of Submitting Author

sroche2@fau.edu

Institution

Florida Atlantic University

Country

USA

ORCID For Submitting Author

0000-0002-3019-2168

Declaration of Conflict of Interest

The authors declare no conflict of interest.

Exports