2023
DOI: 10.1002/adsc.202300261
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Gold(I)‐Catalyzed Cascade Cyclization of Nitrogen or Oxygen Containing Nucleophile Tethered‐Vinylidenecyclopropanes to Pyrrole, Furan, Pyrrolidine and Piperidine Skeletons

Abstract: In this paper, we report a gold(I)catalyzed cascade cyclization of N-or O-nucleophile tethered-vinylidenecyclopropanes (VDCPs), resulting in the synthesis of pyrrole, furan, pyrrolidine, and piperidine skeletons in 30%-98% yields. Depending on the carbon chain length connecting the nucleophile and VDCPs, two reaction pathways are available, leading to different products. Both αamino VDCPs and α-hydroxyl VDCPs, where nucleophiles and VDCPs are connected by a methylene group, undergo intramolecular nucleophilic … Show more

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Cited by 3 publications
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“…Meanwhile, the Yang group reported a CuBr-catalyzed selective synthesis of cyclohexanone-fused pyrroles through the substituent-controlled cyclization of O -acyl oximes with cyclic 1,3-diones . Besides, other transition metal catalysts including Au, Pd, Ag, Rh, and Ru have also been employed in pyrrole synthesis. Although these advances are useful, large amounts of solvents, external heating, long reaction time, and/or highly functionalized starting materials are often required, which will limit the practicability of these methods.…”
mentioning
confidence: 99%
“…Meanwhile, the Yang group reported a CuBr-catalyzed selective synthesis of cyclohexanone-fused pyrroles through the substituent-controlled cyclization of O -acyl oximes with cyclic 1,3-diones . Besides, other transition metal catalysts including Au, Pd, Ag, Rh, and Ru have also been employed in pyrrole synthesis. Although these advances are useful, large amounts of solvents, external heating, long reaction time, and/or highly functionalized starting materials are often required, which will limit the practicability of these methods.…”
mentioning
confidence: 99%