Citation: Min Wu, Hui Gao, Huiying Xu, Wei Yi, Zhi Zhou. Enantioselective synthesis of indenopyrazolopyrazolones enabled by dual directing groups-assisted and rhodium(Ⅲ)-catalyzed tandem C-H alkenylation/[3 + 2] stepwise cycloaddition[J]. Chinese Chemical Letters, ;2022, 33(2): 842-846. doi: 10.1016/j.cclet.2021.08.004 shu

Enantioselective synthesis of indenopyrazolopyrazolones enabled by dual directing groups-assisted and rhodium(Ⅲ)-catalyzed tandem C-H alkenylation/[3 + 2] stepwise cycloaddition

Min Wu ¹ ,
Hui Gao ¹ ,
Huiying Xu ,
Wei Yi ^*, ,
Zhi Zhou ^*,

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Protein Modification and Degradation & Molecular Target and Clinical Pharmacology, State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou 511436, China

yiwei@gzhmu.edu.cn

zhouzhi@gzhmu.edu.cn

Received Date: 18 June 2021
Revised Date: 1 August 2021
Accepted Date: 2 August 2021
Available Online: 8 August 2021

Figures(6)

The Cp^XRh(Ⅲ)-catalyzed asymmetric cascade C-H coupling/intramolecular cyclization of azomethine imines with propargyl carbonates has been developed, affording a variety of chiral tetracyclic indenopyrazolopyrazolone frameworks with good substrate/functional group tolerance and enantioselectivity (up to 97:3 er). Combined experimental studies and DFT calculations revealed the Rh(Ⅲ)-catalyzed stepwise annulation process and clarified the synergy coordination mode of dual directing groups in tuning the selectivity.
- Indenopyrazolopyrazolone,
- Azomethine imine,
- Enantioselective synthesis,
- DFT calculations,
- Rhodium(Ⅲ) catalysis
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