The Close Interaction of a C−F Bond with an Amide Carbonyl: Crystallographic and Spectroscopic Characterization

• DOI: 10.1002/anie.202207966
• Publication Date: 2022-06-18T19:59:29Z
• Authors: Stefan Andrew Harry; Muhammad Kazim; Phuong Minh Nguyen; Andrea Zhu; Michael Richard X...; Jonathan Catazaro; Maxime Siegler; Thomas Lectka
• Keywords: Amide; Characterization; Peptide bond

The putative interaction of a C-F bond with an amide carbonyl has been intriguing topic interest in this century for reasons spanning basic physical organic chemistry to biochemistry. However, date, there exist no examples close, well-defined which its unique aspects can be identified and exploited. Herein, we finally present engineered system possessing exceptionally tight C-F-amide interaction, allowing us obtain spectroscopic, crystallographic, kinetic details distinctive, biochemically relevant chemical the first time. In turn, also explore Lewis acid coordination, promotion isomerization, enantiomerization, ion protonation processes.