Optically-active diamide derivatives

Details Optically-active diamide derivatives Optically-active diamide derivatives

C - Chemistry, Metallurgy

07

D

260/304, 260/243

C07D 277/16 (2006.01) C07D 263/16 (2006.01) C07D 265/08 (2006.01) C07D 279/06 (2006.01) C07D 295/185 (2006.01) C07D 417/06 (2006.01)

Patent

CA 1184178

ABSTRACT OF THE DISCLOSURE A novel optically active diamide derivative repre- sented by the following general formula is provided, which is useful as a starting material for asymmetric synthesis of optically active compounds, Image wherein: R1 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; R2 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 stereo- chemical interaction thereof with the substituent R1, the steric configuration of the two asymmetric carbon atoms to which the R2 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 hydroly- sis.

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