Rh(III)-Catalyzed spiroannulation of ketimines with cyclopropenones via sequential C-H/C-C bond activation

An unprecedented Rh(III)-catalyzed [3+3]-spiroannulation of ketimines with cyclopropenones to access spiro[4,5]dienones has been developed. Sequential C-H/C-C bond activation and subsequent nucleophilic addition are disclosed in this process. This procedure represents the first example of the constr...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-04, Vol.58 (30), p.4743-4746
Main Authors: Hu, Hong, Li, Bin-Shi, Xu, Jing-Lei, Sun, Wei, Wang, Yong, Sun, Meng
Format: Article
Language:English
Subjects:
Catalysis
Covalent bonds
Functional groups
Imines
Rhodium - chemistry
Selectivity
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Summary:An unprecedented Rh(III)-catalyzed [3+3]-spiroannulation of ketimines with cyclopropenones to access spiro[4,5]dienones has been developed. Sequential C-H/C-C bond activation and subsequent nucleophilic addition are disclosed in this process. This procedure represents the first example of the construction of spirolactams utilising cyclopropenones as 3C synthons. The remarkable advantages of this protocol are excellent chemo- and regio-selectivity, wide functional group tolerance, high reaction yields, and tolerance towards H O.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc00421f