Gold-Catalyzed Atom-Economic Synthesis of Sulfone-Containing Pyrrolo[2,1‑a]isoquinolines from Diynamides: Evidence for Consecutive Sulfonyl Migration
journal contributionposted on 13.02.2019, 00:00 by Jibing Liu, Pushkin Chakraborty, Heng Zhang, Liang Zhong, Zhi-Xiang Wang, Xueliang Huang
A gold-catalyzed cascade reaction of conjugated diynamides has been developed. In this way, a series of sulfone-containing pyrrolo[2,1-a]isoquinolines featuring the core structural motifs of lamellarin alkaloids were prepared atom economically. Mechanistic studies including DFT calculations uncovered a consecutive 1,2-migration of the sulfonyl group for the formation of a pyrrole ring.
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Consecutive Sulfonyl MigrationmotifseriesPyrrolopyrrole ringmigrationpyrrolosulfone-containingsulfonyl groupcoreDFT calculationsMechanistic studieslamellarin alkaloidsisoquinolineformationDiynamideGold-Catalyzed Atom-Economic SynthesisSulfone-ContainingEvidencediynamidegold-catalyzed cascade reaction