Halide Abstraction-Mediated Synthesis of a Highly Twisted Amide.

J Org Chem

X-ray Crystallography Center, Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States.

Published: September 2024


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Article Abstract

Highly strained [3.2.1] bicyclic twisted amide and corresponding amidium were synthesized for the first time through Ag(I)-mediated halide abstraction. After initial lactamization attempts failed, a second-generation strategy was devised to target amidium via intramolecular alkylation. The 3,4-dihydroisoquinolone cyclization precursor was regioselectively prepared via a Rh(III)-catalyzed C-H activation/annulation reaction. After Ag(I)-assisted cyclization, the [3.2.1] bicyclic framework of amidium was confirmed by X-ray crystallography and enabled full solution characterization of twisted amide .

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11382264PMC
http://dx.doi.org/10.1021/acs.joc.4c01192DOI Listing

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