Gold-Catalyzed Addition of β-Oxo Enols at Tethered Alkynes via a Non-Conia-ene Pathway: Observation of a Formal 1,3-Hydroxymethylidene Migration

Akshay Subhash Narode, Yeu Shiuan Ho, Mu Jeng Cheng, Rai Shung Liu

研究成果: Article同行評審

3 引文 斯高帕斯(Scopus)

摘要

With the relay process of Ag(I)/Au(I) catalysts, a one-pot synthesis of skeletally rearranged (1-hydroxymethylidene)indene derivatives from 2-alkynylbenzaldehydes and α-diazo esters is described. This cascade sequence involves Au(I)-catalyzed 5-endo-dig attack of highly enolizable aldehydes at the tethered alkynes, leading to carbocyclizations with a formal 1,3-hydroxymethylidene transfer. On the basis of density functional theory calculations, the mechanism likely involves formation of cyclopropylgold carbenes, followed by an appealing 1,2-cyclopropane migration.

原文English
頁(從 - 到)1589-1594
頁數6
期刊Organic Letters
25
發行號9
DOIs
出版狀態Published - 2023 3月 10

All Science Journal Classification (ASJC) codes

  • 生物化學
  • 物理與理論化學
  • 有機化學

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