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Catalytic Asymmetric Dearomatization by Visible-Light-Activated [2+2] Photocycloaddition

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Title
Catalytic Asymmetric Dearomatization by Visible-Light-Activated [2+2] Photocycloaddition
Author(s)
Naifu Hu; Hoimin Jung; Yu Zheng; Juhyeong Lee; Lilu Zhang; Zakir Ullah; Xiulan Xie; Klaus Harms; Mu-Hyun Baik; Eric Meggers
Subject
asymmetric catalysis, ; cycloaddition, ; dearomatization, ; photochemistry, ; rhodium
Publication Date
2018-05
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.57, no.21, pp.6242 - 6246
Publisher
WILEY-V C H VERLAG GMBH
Abstract
A novel method for the catalytic asymmetric dearomatization by visible-light-activated [2+2] photocycloaddition with benzofurans and one example of a benzothiophene is reported, thereby providing chiral tricyclic structures with up to four stereocenters including quaternary stereocenters. The benzofurans and the benzothiophene are functionalized at the 2-position with a chelating N-acylpyrazole moiety which permits the coordination of a visible-light-activatable chiral-at-rhodium Lewis acid catalyst. Computational molecular modeling revealed the origin of the unusual regioselectivity and identified the heteroatom in the heterocycle to be key for the regiocontrol ⓒ 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
https://pr.ibs.re.kr/handle/8788114/5924
DOI
10.1002/anie.201802891
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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