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The [4 + 2] cyclization/retro-Mannich reaction cascade of para-quinone methide derivatives with Pd-containing 1,4-dipoles

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Abstract

The first [4 + 2] cyclization/retro-Mannich reaction cascade of para-quinone methides with Pd-containing 1,4-dipoles generated in situ from vinyl benzoxazinanones has been established. The corresponding rearrangement products were obtained in generally good to excellent yields (up to 92% yield). This reaction represents the first example of C[double bond, length as m-dash]C double bond cleavage of para-quinone methides, which will greatly enrich the chemistry of quinone methides.

Graphical abstract: The [4 + 2] cyclization/retro-Mannich reaction cascade of para-quinone methide derivatives with Pd-containing 1,4-dipoles

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Publication details

The article was received on 30 May 2018, accepted on 05 Sep 2018 and first published on 06 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB01274A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    The [4 + 2] cyclization/retro-Mannich reaction cascade of para-quinone methide derivatives with Pd-containing 1,4-dipoles

    X. Jiang, S. Wu, J. Wang, H. Lu, G. Mei and F. Shi, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01274A

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