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Issue 3, 2010
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Stereoselective synthesis of trans- and cis-2-aryl-3-(hydroxymethyl)aziridines through transformation of 4-aryl-3-chloro-β-lactams and study of their ring opening

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Abstract

trans- and cis-1-Alkyl-4-aryl-3-chloroazetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were transformed into the corresponding non-activated trans- and cis-2-aryl-3-(hydroxymethyl)aziridines via reductive ring contraction using LiAlH4 in Et2O. Furthermore, trans-2-aryl-3-(hydroxymethyl)aziridines were transformed into 2-amino-3-arylpropan-1-ols and anti-2-amino-3-aryl-3-methoxypropan-1-ols by means of an unprecedented ring opening by LiAlH4 and by MeOH, respectively. cis-2-Aryl-3-(hydroxymethyl)aziridines were shown to be highly reluctant to undergo ring opening by LiAlH4 and MeOH under similar reaction conditions.

Graphical abstract: Stereoselective synthesis of trans- and cis-2-aryl-3-(hydroxymethyl)aziridines through transformation of 4-aryl-3-chloro-β-lactams and study of their ring opening

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Publication details

The article was received on 23 Sep 2009, accepted on 26 Oct 2009 and first published on 04 Dec 2009


Article type: Paper
DOI: 10.1039/B919864D
Org. Biomol. Chem., 2010,8, 607-615

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    Stereoselective synthesis of trans- and cis-2-aryl-3-(hydroxymethyl)aziridines through transformation of 4-aryl-3-chloro-β-lactams and study of their ring opening

    M. D'hooghe, K. Mollet, S. Dekeukeleire and N. De Kimpe, Org. Biomol. Chem., 2010, 8, 607
    DOI: 10.1039/B919864D

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