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Catalytic Asymmetric Dearomatization by Visible‐Light‐Activated [2+2] Photocycloaddition |
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| Authors: | Dr Naifu Hu Hoimin Jung Yu Zheng Juhyeong Lee Dr Lilu Zhang Zakir Ullah Dr Xiulan Xie Dr Klaus Harms Prof?Dr Mu‐Hyun Baik Prof?Dr Eric Meggers |
| Institution: | 1. Fachbereich Chemie, Philipps-Universit?t Marburg, Marburg, Germany;2. Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, Republic of Korea;3. Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, Republic of Korea |
| 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. |
| Keywords: | asymmetric catalysis cycloaddition dearomatization photochemistry rhodium |