Optically-active diamide derivatives.

摘要

A novel optically active diamide derivative represented by the following general formula is provided, which is useful as a starting material for asymmetric synthesis of optically active compounds.
<Chemistry id="chema01" num="0001"><Image id="ia01" he="28" wi="73" file="IMGA0001.TIF" imgContent="chem" imgFormat="TIFF" inline="no" /></Chemistry>wherein: R is an acyclic or cyclic, divalent atomic group containing at least one carbon atom which will, upon substitution of one of the heterocyclic groups in the formula with a nucleophilic reagent, stand as an asymmetric center in the substitution product; R<Sup>2</Sup> is a substituent which has such a configuration and a molecular size that the regioselectivity in the substitution reaction of the heterocyclic group with the nucleophilic reagent can be determined by a stereochemical interaction thereof with the substituent R<Sup>1</Sup>, the steric configuration of the two asymmetric carbon atoms to which the R<Sup>2</Sup> substituents are attached being identical; X is a sulfur atom or an oxygen atom; and n is an integer which is 1 or 2. Such a diamide derivative can be prepared by subjecting the corresponding dicarboxylic acid or an anhydride thereof with the corresponding heterocyclic compound to condensation reaction in the presence of a condensation agent.

The optically-active diamide derivative can be used in the reaction with a nucleophilic reagent to obtain an optically-active compound. The resulting compound can be further modified by subjecting it to reaction with other nucleophilic reagent or to hydrolysis.