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The Mechanistic Basis for Electronic Effects on Enantioselectivity in the (salen)Mn(III)-Catalyzed Epoxidation Reaction

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Contribution from the Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138
Cite this: J. Am. Chem. Soc. 1998, 120, 5, 948–954
Publication Date (Web):January 8, 1998
https://doi.org/10.1021/ja973468j
Copyright © 1998 American Chemical Society
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Abstract

Enantioselectivity in the (salen)Mn-catalyzed asymmetric epoxidation reaction correlates directly with the electronic properties of the ligand substituents, with complexes bearing electron-donating substituents affording highest ee's. Several lines of evidence point to a single factorcontrol of the position of the transition state along the reaction coordinateas being responsible for the electronic effects on enantioselectivity. Analysis of the epoxidation of cis-β-deuteriostyrene reveals that electron-rich catalysts display a more pronounced secondary inverse isotope effect than electron-deficient catalysts. A strong correlation between ΔΔH⧧ and the electronic character of the catalyst is also observed. The conclusion that enantioselectivity is tied to the position of a transition state along the reaction coordinate may hold general implications for the design of asymmetric catalysts, particularly those that effect reactions without substrate precoordination.

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