Expedite Protocol for Construction of ChiralRegioselectively N-Protected MonosubstitutedPiperazine, 1,4-Diazepane, and 1,4-DiazocaneBuilding Blocks

摘要

This paper describes the first study of solution-phasesynthesis of chiral monosubstituted piperazine buildingblocks from nosylamide-activated aziridines. The proto-col, involving aminolysis of the starting aziridines withω-amino alcohols and subsequent Fukuyama-Mitsunobucyclization, offers the advantage of mild conditions aswell as short reaction times, and it leads to optically pureN-Boc- or N-Ns-protected piperazines. This four-stepsequence, requiring only a single final chromatographicpurification, was extended to include novel diazepane anddiazocane derivatives.