4.8 Article

Hydroxyl-directed C-H carbonylation enabled by mono-N-protected amino acid ligands: An expedient route to 1-isochromanones

Journal

CHEMICAL SCIENCE
Volume 2, Issue 5, Pages 967-971

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c0sc00633e

Keywords

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Funding

  1. TSRI
  2. US NSF [NSF CHE1011898]
  3. China Scholarship Council
  4. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University
  5. A*STAR
  6. US NSF
  7. US DOD
  8. Skaggs-Oxford Scholarship Program for predoctoral fellowships

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A Pd(II)-catalyzed C-H carbonylation protocol of phenethyl alcohols has been developed using amino acid ligands to promote the reaction. This transformation provides an expedient route to 1-isochromanone motifs, which are common structural elements in natural products and other biologically active compounds. A concise synthesis of a histamine release inhibitor showcases the utility of this transformation.

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