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Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of
Jennifer M Crawford1, Elizabeth A Stone2, Anthony J Metrano2
1Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.
Abstract:
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.
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