A general method for the facile synthesis of optically active 2-substituted piperazines via functionalized 2,5-diketopiperazines
2014
Abstract Upon utilization of some common methods described in the literature for the synthesis of chiral, 2-substituted
2,5-diketopiperazines, extensive
racemizationwas observed. Further investigation showed that heating in the presence of a mild base
racemizedthe chiral center in the product
diketopiperazines. A generalized, readily scalable route was sought and, after investigating the effect of base and temperature, conditions were identified that promoted cyclization without erosion of
enantiomeric excess. An array of functionalization was tolerated and this procedure serves as a useful and reliable method for the facile synthesis of this important class of compounds.
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