Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 130, Issue 8, Pages 762-765Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2009.06.004
Keywords
Trifluoromethylation; Crown ethers; Chiral catalysis; Enantioselective; Phase-transfer catalysts
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Funding
- KAKENHI
- Ministry of Education, Culture, Sports, Science and Technology Japan
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Synthesis of novel C2-symmetric chiral crown ethers and their application to enantioselective trifluoromethylation of aldehydes and ketones are discussed. The use of a series of C2-symmetric chiral crown ethers 2 or 3 derived from commercially available (R)-1,1'-bi-2-naphthol for the enantioselective trifluoromethylation of 2-naphthyl aldehyde 1a with (trifluoromethyl)trimethylsilane in the presence of a base was attempted. Iodo-substituted crown ether 2b was found to be the most effective in the model reaction. Moderate enantioselectivities were observed for the trifluoromethylation of both aryl or alkyl aldehydes and alkyl aryl ketones in 21-44% ees. Although the ees are still improvable, this is the first example of a chiral crown ether-catalyzed enantioselective trifluoromethylation reaction. (C) 2009 Elsevier B.V. All rights reserved.
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