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Adv Synth Catal. 2015 Jul 6;357(10):2301-2309. Epub 2015 Jul 14.

A Synergistic Combinatorial and Chiroptical Study of Peptide Catalysts for Asymmetric Baeyer-Villiger Oxidation.

Author information

1
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States, ;
2
Department of Chemistry, The University of Texas at Austin, Austin, Texas 78712, United States, ;

Abstract

We report an approach to the asymmetric Baeyer-Villiger oxidation utilizing bioinformatics-inspired combinatorial screening for catalyst discovery. Scaled-up validation of our on-bead efforts with a circular dichroism-based assay of alcohols derived from the products of solution-phase reactions established the absolute configuration of lactone products; this assay proved equivalent to HPLC in its ability to evaluate catalyst performance, but was far superior in its speed of analysis. Further solution-phase screening of a focused library suggested a mode of asymmetric induction that draws distinct parallels with the mechanism of Baeyer-Villiger monooxygenases.

KEYWORDS:

Baeyer-Villiger oxidation; catalysis; circular dichroism; peptides

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