Pyrones to Pyrans:  Enantioselective Radical Additions to Acyloxy Pyrones

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Abstract

This paper describes a highly site-, diastereo-, and enantioselective intermolecular radical addition/hydrogen atom transfer to hydroxypyrone pyromeconic and kojic acids. The methodology can be extended to the formation of chiral quaternary centers. The products obtained are densely functionalized pyran moieties. The products contain structural features amenable for the introduction of additional substituents.

Citing Articles

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

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  • Update 1 of: C₂-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis

    Giovanni Desimoni, Giuseppe Faita, and Karl Anker Jørgensen
    Chemical Reviews2011 111 (11), PR284-PR437
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Diastereoselective Tin-Free Tandem Radical Additions to 3-Formylchromones

  Jake R. Zimmerman, Madhuri Manpadi, Russell Spatney, and Aaron Baker
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    The Journal of Organic Chemistry2011 76 (19), 8076-8081

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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Enantioselective Radical Conjugate Addition to α′-Phosphoric Enones

  Sunggi Lee and Sunggak Kim
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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
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  Structure Revision and Synthesis of a Novel Labdane Diterpenoid from Zingiber ottensii

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    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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