Rhodium(I)-Catalyzed Asymmetric Hydroarylative Cyclization of 1,6-Diynes to Access Atropisomerically Labile Chiral Dienes
Panjie Hu
School of Chemistry and Chemical Engineering, Shaanxi Normal University (SNNU), Xi'an, 710062 China
Search for more papers by this authorLingfei Hu
School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 China
Search for more papers by this authorDr. Xiao-Xi Li
Institute of Molecular Science and Engineering, Institute of Frontier and Interdisciplinary Sciences, Shandong University, Qingdao, 266237 China
Search for more papers by this authorMengxiao Pan
School of Chemistry and Chemical Engineering, Shaanxi Normal University (SNNU), Xi'an, 710062 China
Search for more papers by this authorCorresponding Author
Dr. Gang Lu
School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xingwei Li
School of Chemistry and Chemical Engineering, Shaanxi Normal University (SNNU), Xi'an, 710062 China
Institute of Molecular Science and Engineering, Institute of Frontier and Interdisciplinary Sciences, Shandong University, Qingdao, 266237 China
Search for more papers by this authorPanjie Hu
School of Chemistry and Chemical Engineering, Shaanxi Normal University (SNNU), Xi'an, 710062 China
Search for more papers by this authorLingfei Hu
School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 China
Search for more papers by this authorDr. Xiao-Xi Li
Institute of Molecular Science and Engineering, Institute of Frontier and Interdisciplinary Sciences, Shandong University, Qingdao, 266237 China
Search for more papers by this authorMengxiao Pan
School of Chemistry and Chemical Engineering, Shaanxi Normal University (SNNU), Xi'an, 710062 China
Search for more papers by this authorCorresponding Author
Dr. Gang Lu
School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xingwei Li
School of Chemistry and Chemical Engineering, Shaanxi Normal University (SNNU), Xi'an, 710062 China
Institute of Molecular Science and Engineering, Institute of Frontier and Interdisciplinary Sciences, Shandong University, Qingdao, 266237 China
Search for more papers by this authorAbstract
Axially chiral open-chained olefins are an underexplored class of atropisomers, whose enantioselective synthesis represents a daunting challenge due to their relatively low racemization barrier. We herein report rhodium(I)-catalyzed hydroarylative cyclization of 1,6-diynes with three distinct classes of arenes, enabling highly enantioselective synthesis of a broad range of axially chiral 1,3-dienes that are conformationally labile (ΔG≠(rac)=26.6–28.0 kcal/mol). The coupling reactions in each category proceeded with excellent enantioselectivity, regioselectivity, and Z/E selectivity under mild reaction conditions. Computational studies of the coupling of quinoline N-oxide system reveal that the reaction proceeds via initial oxidative cyclization of the 1,6-diyne to give a rhodacyclic intermediate, followed by σ-bond metathesis between the arene C−H bond and the Rh−C(vinyl) bond, with subsequent C−C reductive elimination being enantio-determining and turnover-limiting. The DFT-established mechanism is consistent with the experimental studies. The coupled products of quinoline N-oxides undergo facile visible light-induced intramolecular oxygen-atom transfer, affording chiral epoxides with complete axial-to-central chirality transfer.
Conflict of interest
The authors declare no conflict of interest.
Open Research
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