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

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

Standard

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.; Franzyk, Henrik.

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

Harvard

Crestey, F, Witt, M, Jaroszewski, JW & Franzyk, H 2009, 'Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks', Journal of Organic Chemistry, vol. 74, no. 15, pp. 5652-5655. https://doi.org/10.1021/jo900441s

APA

Crestey, F., Witt, M., Jaroszewski, J. W., & Franzyk, H. (2009). Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks. Journal of Organic Chemistry, 74(15), 5652-5655. https://doi.org/10.1021/jo900441s

Vancouver

Crestey F, Witt M, Jaroszewski JW, Franzyk H. Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks. Journal of Organic Chemistry. 2009 Jun 11;74(15):5652-5655. https://doi.org/10.1021/jo900441s

Author

Crestey, François ; Witt, Matthias ; Jaroszewski, Jerzy W. ; Franzyk, Henrik. / Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks. In: Journal of Organic Chemistry. 2009 ; Vol. 74, No. 15. pp. 5652-5655.

Bibtex

@article{06cad441c589429c97d6bfafb4185f24,
title = "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 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.",
author = "Fran{\c c}ois Crestey and Matthias Witt and Jaroszewski, {Jerzy W.} and Henrik Franzyk",
year = "2009",
month = jun,
day = "11",
doi = "10.1021/jo900441s",
language = "English",
volume = "74",
pages = "5652--5655",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "15",

}

RIS

TY - JOUR

T1 - Expedite Protocol for Construction of Chiral Regioselectively N-Protected Monosubstituted Piperazine, 1,4-Diazepane, and 1,4-Diazocane Building Blocks

AU - Crestey, François

AU - Witt, Matthias

AU - Jaroszewski, Jerzy W.

AU - Franzyk, Henrik

PY - 2009/6/11

Y1 - 2009/6/11

N2 - 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.

AB - 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.

U2 - 10.1021/jo900441s

DO - 10.1021/jo900441s

M3 - Journal article

C2 - 19518106

VL - 74

SP - 5652

EP - 5655

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -

ID: 160060737