Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis

Graham Haun; Alyson N. Paneque; David W. Almond; Brooke E. Austin; Gustavo Moura-Letts

doi:10.1021/acs.orglett.9b00097

Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis

Graham Haun, Alyson N. Paneque, David W. Almond, Brooke E. Austin, Gustavo Moura-Letts

Chemistry

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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) ₃ Cl ₂ in high yields and selectivities. Evidence indicates that the proposed redox-neutral pathway is the predominant photoredox mechanism for this transformation.

Original language	English (US)
Pages (from-to)	1388-1392
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.9b00097
State	Published - Mar 1 2019

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis",

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) 3 Cl 2 in high yields and selectivities. Evidence indicates that the proposed redox-neutral pathway is the predominant photoredox mechanism for this transformation. ",

author = "Graham Haun and Paneque, {Alyson N.} and Almond, {David W.} and Austin, {Brooke E.} and Gustavo Moura-Letts",

note = "Funding Information: This material is based upon work supported by the National Science Foundation CAREER award under grant number CHE-1752085. We are also thankful to Dr. John F. Eng at Princeton University for his help with HRMS analysis. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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AU - Almond, David W.

AU - Austin, Brooke E.

AU - Moura-Letts, Gustavo

N1 - Funding Information: This material is based upon work supported by the National Science Foundation CAREER award under grant number CHE-1752085. We are also thankful to Dr. John F. Eng at Princeton University for his help with HRMS analysis. Publisher Copyright: © 2019 American Chemical Society.

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Y1 - 2019/3/1

N2 - 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) 3 Cl 2 in high yields and selectivities. Evidence indicates that the proposed redox-neutral pathway is the predominant photoredox mechanism for this transformation.

AB - 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) 3 Cl 2 in high yields and selectivities. Evidence indicates that the proposed redox-neutral pathway is the predominant photoredox mechanism for this transformation.

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Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis

Abstract

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