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Gold-Catalyzed Stereoselective Domino Cyclization/Alkynylation of N-Propargylcarboxamides with Benziodoxole Reagents for the Synthesis of Alkynyloxazolines

Zhao, X., Tian, B., Yang, Y., Si, X., Mulks, F. F., Rudolph, M., Rominger, F. & Hashmi, A. S. K., 2-Jul-2019, In : Advanced Synthesis & Catalysis. 361, 13, p. 3155-3162 8 p.

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  • Gold-Catalyzed Stereoselective Domino Cyclization/Alkynylation of N-Propargylcarboxamides with Benziodoxole Reagents

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DOI

  • Ximei Zhao
  • Bing Tian
  • Yangyang Yang
  • Xiaojia Si
  • Florian F. Mulks
  • Matthias Rudolph
  • Frank Rominger
  • A. Stephen K. Hashmi

A concise and highly stereoselective synthesis of alkynyloxazolines via a gold-catalyzed domino cyclization-alkynylation cascade of N-propargylcarboxamides with benziodoxole reagents is reported. This new protocol, which represents an attractive alternative to two step sequences based on Sonagashira couplings, offers a broad substrate scope, excellent functional group tolerance, and perfect stereoselectivity. A comparison of the computed energies of the isomers of the product suggests kinetic control as the cause of the observed selectivity.

Original languageEnglish
Pages (from-to)3155-3162
Number of pages8
JournalAdvanced Synthesis & Catalysis
Volume361
Issue number13
Publication statusPublished - 2-Jul-2019

    Keywords

  • benziodoxole, gold catalysis, oxazolines, oxidative alkynylation, propargylamides, HYPERVALENT IODINE REAGENTS, DIRECT ALKYNYLATION, PROPARGYLIC AMIDES, CYCLIZATION, OXAZOLES, EFFICIENT, HYDROGENATION, COMPLEXES, INSIGHTS, LIGANDS

ID: 118491627