Expedite protocol for construction of chiral regioselectively N-protected monosubstituted piperazine, 1,4-diazepane, and 1,4-diazocane building blocks.

Abstract

This paper describes the first study of solution-phase synthesis of chiral monosubstituted piperazine building blocks from nosylamide-activated aziridines. The protocol, involving aminolysis of the starting aziridines with omega-amino alcohols and subsequent Fukuyama-Mitsunobu cyclization, offers the advantage of mild conditions as well as short reaction times, and it leads to optically pure N-Boc- or N-Ns-protected piperazines. This four-step sequence, requiring only a single final chromatographic purification, was extended to include novel diazepane and diazocane derivatives.

DOI: 10.1021/jo900441s

Cite this paper

@article{Crestey2009ExpeditePF, title={Expedite protocol for construction of chiral regioselectively N-protected monosubstituted piperazine, 1,4-diazepane, and 1,4-diazocane building blocks.}, author={François Crestey and Matthias Witt and Jerzy W. Jaroszewski and Henrik Franzyk}, journal={The Journal of organic chemistry}, year={2009}, volume={74 15}, pages={5652-5} }