TANDEM ACYL-CLAISEN REARRANGEMENT IN THE PREPARATION OF CHIRAL PRODUCTS

摘要

A novel tandem acyl-Claisen rearrangement reaction is provided. An allylic reactant such as an allylic amine or an allylic thioether, having at least two functional groups that enable the reactant to undergo at least two successive Claisen rearrangement reactions, is reacted with an acid chloride in the presence of a Lewis acid catalyst composition composed of a Lewis acid and a second catalyst component 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.