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Issue 15, 2007
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Regiochemical switching of Mitsunobu cyclisation mode of vicinal diamines with pendant hydroxyl group

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Abstract

Ambident 1,2-diamines derived from the nitro-Mannich reaction containing both a tosyl amide and a secondary amine could be regioselectively cyclised through the tosyl amide onto a pendant primary hydroxyl group to give piperazine (60–75% yields) or 1,4-diazepane (71% yield) ring systems under Mitsunobu conditions. For some substrates addition of Et3N·HCl encouraged regioselective cyclisation through the secondary amine leading to aziridine ring systems.

Graphical abstract: Regiochemical switching of Mitsunobu cyclisation mode of vicinal diamines with pendant hydroxyl group

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Publication details

The article was received on 03 Apr 2007, accepted on 04 Jun 2007 and first published on 22 Jun 2007


Article type: Paper
DOI: 10.1039/B705081J
Citation: Org. Biomol. Chem., 2007,5, 2413-2422
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    Regiochemical switching of Mitsunobu cyclisation mode of vicinal diamines with pendant hydroxyl group

    J. C. Anderson and H. A. Chapman, Org. Biomol. Chem., 2007, 5, 2413
    DOI: 10.1039/B705081J

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