Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks

François Crestey; Matthias Witt; Jerzy W. Jaroszewski; Henrik Franzyk

doi:10.1021/jo900441s

Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks

François Crestey, Matthias Witt, Jerzy W. Jaroszewski, Henrik Franzyk

43 Citations (Scopus)

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 ω-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.

Original language	English
Journal	Journal of Organic Chemistry
Volume	74
Issue number	15
Pages (from-to)	5652-5655
ISSN	0022-3263
DOIs	https://doi.org/10.1021/jo900441s
Publication status	Published - 11 Jun 2009

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Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks. / Crestey, François; Witt, Matthias; Jaroszewski, Jerzy W. et al.

In: Journal of Organic Chemistry, Vol. 74, No. 15, 11.06.2009, p. 5652-5655.

Research output: Contribution to journal › Journal article › Research › peer-review

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Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks

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