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Chemoselective asymmetric dearomative [3 + 2] cycloaddition reactions of purines with aminocyclopropanes

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Abstract

Chemoselective asymmetric [3 + 2] cycloaddition reactions of purines with aminocyclopropanes for the dearomatization of purines have been successfully developed. In the presence of a copper complex, derived from Cu(OTf)2 and bisoxazoline, a series of hydropyrrolo-purine compounds were obtained in high yields (up to 98%) with excellent enantioselectivities (up to 99% ee). The chemoselectivity in current cycloaddition reactions has been explained by density functional theory calculations.

Graphical abstract: Chemoselective asymmetric dearomative [3 + 2] cycloaddition reactions of purines with aminocyclopropanes

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Publication details

The article was received on 09 Jan 2019, accepted on 07 Feb 2019 and first published on 09 Feb 2019


Article type: Research Article
DOI: 10.1039/C9QO00039A
Citation: Org. Chem. Front., 2019, Advance Article

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    Chemoselective asymmetric dearomative [3 + 2] cycloaddition reactions of purines with aminocyclopropanes

    E. Hao, D. Fu, D. Wang, T. Zhang, G. Qu, G. Li, Y. Lan and H. Guo, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00039A

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