Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer

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We report the enantioselective [2+2] cycloaddition of simple cinnamate esters, the products of which are useful synthons for the controlled assembly of cyclobutane natural products. This method utilizes a cocatalytic system in which a chiral Lewis acid accelerates the transfer of triplet energy from an excited-state Ir(III) photocatalyst to the cinnamate ester. Computational evidence indicates that the principal role of the Lewis acid cocatalyst is to lower the absolute energies of the substrate frontier molecular orbitals, leading to greater electronic coupling between the sensitizer and substrate and increasing the rate of the energy transfer event. These results suggest Lewis acids can have multiple beneficial effects on triplet sensitization reactions, impacting both the thermodynamic driving force and kinetics of Dexter energy transfer.
Publisher
AMER CHEMICAL SOC
Issue Date
2019-06
Language
English
Article Type
Article
Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.141, no.24, pp.9543 - 9547

ISSN
0002-7863
DOI
10.1021/jacs.9b04643
URI
http://hdl.handle.net/10203/263236
Appears in Collection
CH-Journal Papers(저널논문)
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