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.
Enantioselective Synthesis of Trifluoromethyl-Substituted 2-Isoxazolines: Asymmetric Hydroxylamine/Enone Cascade Reaction†
Article first published online: 7 JUL 2010
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 49, Issue 33, pages 5762–5766, August 2, 2010
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
- Issue published online: 28 JUL 2010
- Article first published online: 7 JUL 2010
- Manuscript Revised: 27 MAY 2010
- Manuscript Received: 7 APR 2010
- KAKENHI. Grant Numbers: 21390030, 22106515
- asymmetric catalysis;
- 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).