Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis

Taoda Shi, Shenghan Teng, Alavala Gopi Krishna Reddy, Xin Guo, Yueteng Zhang, Kohlson T. Moore, Thomas Buckley, Damian J. Mason, Wei Wang, Eli Chapman, Wenhao Hu

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

We report a bifunctional Ag catalyst promoted intramolecular capture of oxonium ylides with alkynes for the enantioselective synthesis of 2,5-dihydrofurans. This represents unprecedented synergistic catalysis of a bifunctional Ag catalyst. Mechanistic studies revealed that [(R)-3,5-DM-BINAP](AgSbF6)2 (9) is likely to be the active catalytic species and that the reaction involves second order kinetics with respect to 9, suggesting that two molecules of 9 are involved in the intramolecular trapping of a Ag-associated oxonium ylide with a Ag-activated alkyne. Based on our mechanistic hypothesis, we further optimized the reaction, rendering a facile approach to 2,5-dihydrofurans in good to excellent yields in a highly chemo- and enantioselective fashion.

Original languageEnglish (US)
Pages (from-to)8737-8744
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number38
DOIs
StatePublished - Jan 1 2019

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Shi, T., Teng, S., Gopi Krishna Reddy, A., Guo, X., Zhang, Y., Moore, K. T., Buckley, T., Mason, D. J., Wang, W., Chapman, E., & Hu, W. (2019). Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis. Organic and Biomolecular Chemistry, 17(38), 8737-8744. https://doi.org/10.1039/c9ob01903k