Support was provided by KAKENHI (21390030, 22106515). The corresponding author thanks the JSPS for financial support of this work in part through a Joint Research Project between Japan and France.
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Communication
Enantioselective Synthesis of Trifluoromethyl-Substituted 2-Isoxazolines: Asymmetric Hydroxylamine/Enone Cascade Reaction†
Article first published online: 7 JUL 2010
DOI: 10.1002/anie.201002065
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Matoba, K., Kawai, H., Furukawa, T., Kusuda, A., Tokunaga, E., Nakamura, S., Shiro, M. and Shibata, N. (2010), Enantioselective Synthesis of Trifluoromethyl-Substituted 2-Isoxazolines: Asymmetric Hydroxylamine/Enone Cascade Reaction. Angew. Chem. Int. Ed., 49: 5762–5766. doi: 10.1002/anie.201002065
- †
Publication History
- Issue published online: 28 JUL 2010
- Article first published online: 7 JUL 2010
- Manuscript Revised: 27 MAY 2010
- Manuscript Received: 7 APR 2010
Funded by
- KAKENHI. Grant Numbers: 21390030, 22106515
- JSPS
Keywords:
- asymmetric catalysis;
- fluorine;
- heterocycles;
- organocatalysis;
- phase-transfer catalysis
Cuts both ways: The title reaction consists of an addition/cyclization/dehydration sequence and affords the biologically important chiral 3,5-diaryl-5-(trifluoromethyl)-2-isoxazolines 1 in excellent yields with high ee values. The flexibility of accessing either the S or R enantiomers of the products has been achieved by the appropriate choice of phase-transfer catalyst (2).