@article{helton_howard_bruno_cartrette_bowles_hearne_proulx_2025, title={Azapeptide Atropisomers From Late-Stage <i>N</i>-Alkylations}, volume={90}, DOI={10.1021/acs.joc.5c01024}, abstractNote={We evaluate peptide sequence compatibility during late-stage azapeptide <i>N</i>-alkylation reactions and describe the atropisomeric properties of the azapeptoid and <i>N</i>1,<i>N</i>2-dialkylated azapeptide products. Our findings indicate that almost all protected amino acid side chains are compatible with the late-stage alkylation conditions on resin, with the exception of methionine. Using variable temperature NMR and dynamic HPLC, N-N rotational energy barriers of 15-16 and 20-24 kcal/mol are reported for a series of azapeptoids (monoalkylated) and <i>N</i>1,<i>N</i>2-dialkylated azapeptides, respectively.}, number={27}, journal={The Journal of Organic Chemistry}, author={Helton, Molly E. and Howard, Christopher S. and Bruno, Keisy Prieto and Cartrette, Katelyn D. and Bowles, Maxwell O. and Hearne, William A. and Proulx, Caroline}, year={2025}, month={Jun}, pages={9549–9558} }