A general method for the facile synthesis of optically active 2-substituted piperazines via functionalized 2,5-diketopiperazines
2014
Ashton, Kate S. | Denti, Mitchell | Norman, Mark H. | St. Jean, David J.
Upon utilization of some common methods described in the literature for the synthesis of chiral, 2-substituted 2,5-diketopiperazines, extensive racemization was observed. Further investigation showed that heating in the presence of a mild base racemized the 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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