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Diastereoselective formal [3 + 3] cycloaddition of isatin-based α-(trifluoromethyl)imines with N,N′-dialkyloxyureas

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Abstract

In the presence of PhI(OH)(OTs) and NaH, the diastereoselective formal [3 + 3] cycloaddition of isatin-based α-(trifluoromethyl)imines with N,N′-dialkyloxyureas proceeded readily, and furnished the relatively trans-configured novel spiro-1,3,5-triazinan-2-ones in reasonable chemical yields. The relative stereochemical configuration of the target products was clearly identified by X-ray diffraction analysis.

Graphical abstract: Diastereoselective formal [3 + 3] cycloaddition of isatin-based α-(trifluoromethyl)imines with N,N′-dialkyloxyureas

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Publication details

The article was received on 25 Sep 2019, accepted on 18 Oct 2019 and first published on 21 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01181A
Org. Chem. Front., 2019, Advance Article

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    Diastereoselective formal [3 + 3] cycloaddition of isatin-based α-(trifluoromethyl)imines with N,N′-dialkyloxyureas

    H. Zhao, J. Guo, L. Wang, W. Ding, Z. Tang, X. Song, H. Wu, X. Fan and X. Bi, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01181A

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