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Article
Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis
Organic Letters (2019)
  • Graham Haun, Rowan University
  • Alyson N. Paneque, Rowan University
  • David W. Almond, Rowan University
  • Brooke E. Austin, Rowan University
  • Gustavo Moura-Letts, Rowan University
Abstract
This effort reports the first redox-neutral visible-light photocatalytic intramolecular dipolar cycloaddition for the diastereoselective synthesis of chromenoisoxazolidines. The authors have found that alkenylphenyl nitrones with a diverse substitution pattern on the aromatic ring and the alkenyl substituent undergo visible-light-promoted cycloadditions in the presence of catalytic amounts of Ru(bpy)3Cl2 in high yields and selectivities. Evidence indicates that the proposed redox-neutral pathway is the predominant photoredox mechanism for this transformation.
Disciplines
Publication Date
March 1, 2019
DOI
10.1021/acs.orglett.9b00097
Citation Information
Graham Haun, Alyson N. Paneque, David W. Almond, Brooke E. Austin, et al.. "Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis" Organic Letters Vol. 21 Iss. 5 (2019) p. 1388 - 1392
Available at: http://works.bepress.com/gustavo-moura-letts/10/