Journal
TETRAHEDRON
Volume 66, Issue 5, Pages 1111-1118Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.11.018
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Funding
- Japan Society for the Promotion of Science (JSPS)
- Global COE Program
- The University of Tokyo
- MEXT, Japan
- Grants-in-Aid for Scientific Research [21225002] Funding Source: KAKEN
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The ring-opening reactions of meso-epoxides with aniline and indole derivatives proceeded smoothly in water in the presence of Zn(II) and Cu(II) surfactant-type catalysts to afford the corresponding products in moderate to high yields with good to excellent enantioselectivities. Opposite enantiomers were obtained by using Sc(III) and Zn(II) or Cu(II) with the same chiral ligand. Crystal structures of these catalysts may explain the reversal of the enantioselectivity. Some reactions were also tested in dichloromethane (DCM), and it was revealed that the reactions proceeded faster in water than in DCM. Finally, several nonlinear effect experiments suggested unique structure of these chiral catalysts. (C) 2009 Elsevier Ltd. All rights reserved.
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