Journal
SCIENCE
Volume 328, Issue 5984, Pages 1376-1379Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1188217
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Funding
- Japan Society for the Promotion of Science [20245022]
- New Energy and Industrial Technology Development Organization
- Shionogi Award in Synthetic Organic Chemistry, Japan
- Ministry of Education, Culture, Sports, Science and Technology
- Grants-in-Aid for Scientific Research [20245022] Funding Source: KAKEN
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It is desirable to minimize the use of rare or toxic metals for oxidative reactions in the synthesis of pharmaceutical products. Hypervalent iodine compounds are environmentally benign alternatives, but their catalytic use, particularly for asymmetric transformations, has been quite limited. We report here an enantioselective oxidative cycloetherification of ketophenols to 2-acyl-2,3-dihydrobenzofuran derivatives, catalyzed by in situ-generated chiral quaternary ammonium (hypo)iodite salts, with hydrogen peroxide as an environmentally benign oxidant. The optically active 2-acyl 2,3-dihydrobenzofuran skeleton is a key structure in several biologically active compounds.
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