Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.
KAUST DepartmentChemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2020-01-31
Print Publication Date2020-02
Permanent link to this recordhttp://hdl.handle.net/10754/661577
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AbstractChiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context.
CitationMei, G.-J., Zheng, W., Gonçalves, T. P., Tang, X., Huang, K.-W., & Lu, Y. (2020). Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles. iScience, 100873. doi:10.1016/j.isci.2020.100873
SponsorsY.L. thanks the Singapore National Research Foundation, Prime Minister’s Office for the NRF Investigatorship Award (R-143-000-A15-281). Financial supports from the National University of Singapore (R-143-000-695-114 & C-141-000-092-001) and the National Natural Science Foundation of China (21672158 & 21702077) are also gratefully acknowledged.
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Mei, Guang-Jian, Zheng, Wenrui, Gonçalves, Théo P., Tang, Xiwen, Huang, Kuo-Wei, & Lu, Yixin. (2020). CCDC 1957145: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC23PKQ3. DOI: 10.5517/ccdc.csd.cc23pkq3 Handle: 10754/664854