Lewis acid-catalyzed claisen rearrangement in the preparation of chiral products
US6359174B1 · kind B1 · utility
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Key dates
| Filing date | Sep 26, 2000 |
| Grant date | Mar 19, 2002 |
| Priority date | — |
| Expiry date | Sep 26, 2020 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07B2200/07
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A novel Claisen rearrangement reaction is provided. An allylic reactant such as an allylic amine, an allylic ether or an allylic thioether is reacted with an acid chloride in the presence of a Lewis acid catalyst composition composed of a Lewis acid and a base selected from the group consisting of tertiary amines and non-nitrogenous bases. The stereochemistry of the reaction product is readily controlled by the positioning and size of substituents on the allylic reactant. The reaction may be carried out on a solid support, i.e., on the surface of a substrate suitable for conducting solid phase chemical reactions.
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