Journal
ORGANIC LETTERS
Volume 17, Issue 19, Pages 4886-4889Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02440
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Funding
- National Natural Sciences Foundation of China [21121062, 21432011, 21272250]
- National Basic Research Program of China (973 Program) [2015CB856600]
- Chinese Academy of Sciences
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A highly enantioselective and regioselective chiral Lewis acid catalyzed tandem Friedel-Crafts/lactonization reaction is reported, providing direct access to plenty of 3-hydroxy-3-trifluoromethyl benzofuran-2-ones in up to 94% yields with up to >99% ee. Mechanistic study reveals that the interactions between the phenolic hydroxyl group and trifluoropyruvate are the most likely contributing factor to the high enantio- and regioselectivity. Optically pure (-)-BHFF can be obtained in gram-scale with 0.05 mol % catalyst, demonstrating the potentially utility of this method in medicinal chemistry.
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