What question did this study set out to answer?

To establish an asymmetric induction method for allylic C–H oxidation in catalytic systems that cannot tolerate strongly coordinating chiral ligands.

July 15, 2008Angewandte Chemie International EditionOpen Access

A Chiral Lewis Acid Strategy for Enantioselective Allylic CH Oxidation

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Authors

DCDustin J. CovellSt. John's University MWM. Christina WhiteUniversity of Illinois Urbana-Champaign

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Implication

Experimental study demonstrates high enantioselectivity in allylic oxidation of terminal olefins, indicating a viable chiral Lewis acid strategy for systems incompatible with coordinating ligands.

Key Points

To establish an asymmetric induction method for allylic C–H oxidation in catalytic systems that cannot tolerate strongly coordinating chiral ligands.
Designed a catalytic system pairing 1,4-benzoquinone with a chiral Lewis acid to effect oxidation of terminal olefins.
Investigated the reaction pathway and mechanism of asymmetric induction in the absence of direct chiral ligand coordination.
Achieved high levels of enantioselectivity for the catalytic allylic C–H oxidation of terminal olefins.
Demonstrated that chiral Lewis acids successfully induce asymmetry in oxidative environments incompatible with traditional chiral ligands.

Cite This Study

Covell et al. (2008) studied this question.

synapsesocial.com/papers/6a86e20c3f44447e627cb5a8 https://doi.org/10.1002/anie.200802106

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Implication

Experimental study demonstrates high enantioselectivity in allylic oxidation of terminal olefins, indicating a viable chiral Lewis acid strategy for systems incompatible with coordinating ligands.

A Chiral Lewis Acid Strategy for Enantioselective Allylic CH Oxidation

Discussion

Member takes

Implication

Key Points

Cite This Study

A Chiral Lewis Acid Strategy for Enantioselective Allylic CH Oxidation

Discussion

Member takes

Implication

Key Points

Cite This Study

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