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Phosphine-catalyzed [4 + 2] cyclization of para-quinone methide derivatives with allenes

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Abstract

The first [4 + 2] cyclization of para-quinone methide (p-QM) derivatives with allenes has been established via phosphine catalysis, which afforded a series of chroman derivatives in high yields (up to 97%) and excellent (E/Z)-selectivities (all >95 : 5 E/Z). This reaction will not only enrich the research contents of cyclization reactions involving p-QM derivatives, but also provide a good example of the application of allenes and phosphine catalysis in cyclization reactions. In addition, this approach also offers a useful method for the construction of chroman scaffolds.

Graphical abstract: Phosphine-catalyzed [4 + 2] cyclization of para-quinone methide derivatives with allenes

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Publication details

The article was received on 29 Nov 2018, accepted on 02 Jan 2019 and first published on 03 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02979B
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Phosphine-catalyzed [4 + 2] cyclization of para-quinone methide derivatives with allenes

    F. Yuan, F. Jiang, K. Chen, G. Mei, Q. Wu and F. Shi, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02979B

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