3 years ago

Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3-Arylquinazolin-4(3H)-ones

Parameterization
and Analysis of Peptide-Based Catalysts
for the Atroposelective Bromination of 3-Arylquinazolin-4(3H)-ones
Scott J. Miller, Elizabeth A. Stone, Jennifer M. Crawford, Anthony J. Metrano, Matthew S. Sigman
We report the development of a method to parameterize and predict the performance of structurally flexible β-turn-containing peptide catalysts, using the atroposelective bromination of 3-arylquinazolin-4(3H)-ones as a case study. The multivariate correlations obtained for tetrapeptides of two β-turn types, type I′ pre-helical and type II′ β-hairpin, indicate that although one conformer may be associated with a more dominant contribution to the observed enantioselectivity, it is possible that multiple conformers contribute to a complex transition state ensemble.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b11303

DOI: 10.1021/jacs.7b11303

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