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

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Title
Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer
Author(s)
Mary Elisabeth Daub; Hoimin Jung; Byung Joo Lee; Joonghee Won; Mu-Hyun Baik; Tehshik P. Yoon
Publication Date
2019-06
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.141, no.24, pp.9543 - 9547
Publisher
AMER CHEMICAL SOC
Abstract
© 2019 American Chemical Society.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 © 2019 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/6066
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
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