4.7 Article

Pd(II)/Norbornene-Catalyzed Meta-C-H Alkylation of Nosyl-Protected Phenylalanines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 21, Pages 13211-13216

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01933

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Funding

  1. National Natural Science Foundation of China [21662017]
  2. Natural Science Foundation of Jiangxi Province of China [20171BAB2030007]

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A Pd/norbornene-catalyzed direct meta-alkylation of nosyl-protected phenylalanine derivatives with alkyl iodides is reported in moderate to good yields. The use of diisopropyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate is identified as a more suitable transient mediator. A simple pyridine ligand is also essential for this reaction to proceed. No racemization was observed in this meta-methylation reaction.

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