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Highly Enantioselective 6π Photoelectrocyclizations Engineered by Hydrogen Bonding

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Title
Highly Enantioselective 6π Photoelectrocyclizations Engineered by Hydrogen Bonding
Author(s)
Swords, Wesley B.; Hanna Lee; Yerin Park; Llamas, Franco; Skubi, Kazimer L.; Jiyong Park; Guzei, Ilia A.; Mu-Hyun Baik; Yoon, Tehshik P.
Publication Date
2023-12
Journal
Journal of the American Chemical Society, v.145, no.49, pp.27045 - 27053
Publisher
American Chemical Society
Abstract
Photochemical electrocyclization reactions are valued for both their ability to produce structurally complex molecules and their central role in elucidating fundamental mechanistic principles of photochemistry. We present herein a highly enantioselective 6π photoelectrocyclization catalyzed by a chiral Ir(III) photosensitizer. This transformation was successfully realized by engineering a strong hydrogen-bonding interaction between a pyrazole moiety on the catalyst and a basic imidazolyl ketone on the substrate. To shed light on the origin of stereoinduction, we conducted a comprehensive investigation combining experimental and computational mechanistic studies. Results from density functional theory calculations underscore the crucial role played by the prochirality and the torquoselectivity in the electrocyclization process as well as the steric demand in the subsequent [1,4]-H shift step. Our findings not only offer valuable guidance for developing chiral photocatalysts but also serve as a significant reference for achieving high levels of enantioselectivity in the 6π photoelectrocyclization reaction. © 2023 American Chemical Society.
URI
https://pr.ibs.re.kr/handle/8788114/14465
DOI
10.1021/jacs.3c10782
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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