Migratory aptitude in the Baeyer-Villiger reaction follows electronic and steric factors
Migratory aptitude in the Baeyer-Villiger reaction is fundamentally dictated by electronic and steric factors, such as the migrating group's ability to stabilize positive charge and the relief of steric strain, though specialized enzymes can sometimes override these classical trends.
The retrieved papers confirm that electronic (cation stability) and steric (relief of non-bonded interactions) factors govern migratory aptitude and regioselectivity in the Baeyer-Villiger reaction. While specialized enzymes or catalysts can override these traditional factors through directed evolution or specific binding pockets, the foundational principles of electronic and steric control remain well-established and supported by multiple studies.
Li G, Garcia-Borràs M, Fürst MJLJ, Ilie A, Fraaije MW, Houk KN, Reetz MT. Overriding Traditional Electronic Effects in Biocatalytic Baeyer-Villiger Reactions by Directed Evolution.. 2018. https://doi.org/10.1021/jacs.8b04742
This study discusses how electronic and steric factors govern Baeyer-Villiger regioselectivity, even though enzymatic directed evolution can sometimes override these traditional effects.
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Mitchell A. Winnik, Valerie Stoute. Steric Effects in the Baeyer–Villiger Reaction of Simple Ketones. 1973. https://doi.org/10.1139/v73-417
Early foundational work specifically details how steric and electronic effects dictate migratory aptitude and selectivity in the Baeyer-Villiger reaction of simple ketones.
Nadia C. Abascal, Scott J. Miller. Solution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer-Villiger Oxidation. 2016. https://doi.org/10.1021/acs.orglett.6b02282
This paper notes a peptide-based catalyst's facility to control both enantioselectivity and migratory aptitude in the Baeyer-Villiger oxidation, confirming the operation of these underlying factors.
Vinod Dave, J. B. Stothers, E. W. Warnhoff. Conformational and steric effects on regioselectivity in the Baeyer–Villiger reaction. 1984. https://doi.org/10.1139/v84-337
This research highlights how steric effects and the relief of non-bonded interactions determine regioselectivity and migratory preference during the Baeyer-Villiger reaction.
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