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Synthesis 2022; 54(02): 499-505
DOI: 10.1055/a-1561-5557
DOI: 10.1055/a-1561-5557
paper
Diastereoselective Palladium-Catalyzed [4+1] Cycloadditions of 4-Vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-ones with In Situ Formed Carbenes
We are grateful for financial support from NSFC (21602094), Natural Science Foundation of Shandong Province (ZR2016BB11), and this work was supported by Taishan Scholar Research Fund of Shandong Province.
Abstract
Herein, we present a palladium-catalyzed tandem [4+1] cycloaddition of 4-vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-ones with N-tosylhydrazones. The reaction is accomplished by merging the in situ generated aza-ortho-quinone methides (aza-o-QMs) with nucleophilic carbenes. This method enables the construction of diverse indolines with broad functional group compatibility in good yields with high levels of diastereoselectivity under mild conditions.
Key words
aza-o-quinone methides - dihydroindole - [4+1] cycloadditions - Pd(0)-catalyzed - benzoxazinones - carbenes◊ These authors contributed equally.
Supporting Information
- Supporting information for this article (Experimental procedure and spectra data (PDF)) is available online at https://doi.org/10.1055/a-1561-5557. CCDC No. 2071407 (3ak) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- Supporting Information
Publication History
Received: 15 June 2021
Accepted after revision: 29 July 2021
Accepted Manuscript online:
29 July 2021
Article published online:
17 September 2021
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Selective examples of reviews of o-QMs see: