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Platinum-Catalyzed Tandem Cycloisomerization Reaction of Benzoendiynyl Esters: Regioselective Long-Range 1,5-Acyl Migration

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journal contribution
posted on 07.11.2014, 00:00 by Zhiyuan Chen, Xuegong Jia, Jiapian Huang, Jianjun Yuan
A PtII-catalyzed intramolecular chemo- and regioselective pentannulation/long-range 1,5-acyl migration reaction is described. This cascade cycloisomerization protocol produces a wide variety of benzofulvene diketones in good to excellent yields with exclusively the Z configuration of the exocyclic double bond of the final product. The 18O isotope experiment together with 13C NMR, HRMS, and HMBC analyses confirmed an interesting long-range acyl rearrangement process in this transformation.

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