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  • Title: Microwave-assisted regioselective ring opening of non-activated aziridines by lithium aluminium hydride.
    Author: Stanković S, D'hooghe M, De Kimpe N.
    Journal: Org Biomol Chem; 2010 Oct 07; 8(19):4266-73. PubMed ID: 20683539.
    Abstract:
    A new synthetic protocol for the LiAlH(4)-promoted reduction of non-activated aziridines under microwave conditions was developed. Thus, ring opening of 2-(acetoxymethyl)aziridines provided the corresponding beta-amino alcohols, which were then used as eligible substrates in the synthesis of 5-methylmorpholin-2-ones via condensation with glyoxal in THF. The same procedure was applied for the preparation of novel 5(R)- and 5(S)-methylmorpholin-2-ones starting from the corresponding enantiopure 2-(hydroxymethyl)aziridines. Additionally, 2-(methoxymethyl)- and 2-(phenoxymethyl)aziridines were treated with LiAlH(4) under microwave irradiation, giving rise to either isopropylamines or 1-methoxypropan-2-amines depending on the reaction conditions.
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