Issue 37, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
30 May 2018
Accepted
05 Sep 2018
First published
06 Sep 2018

Org. Biomol. Chem., 2018,16, 8395-8402

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, 16, 8395 DOI: 10.1039/C8OB01274A

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