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  • Title: Total selective synthesis of enantiopure O1-acyl-3-aminoalkane-1,2-diols by ring opening of aminoepoxides with carboxylic acids.
    Author: Concellón JM, Suárez JR, del Solar V, Llavona R.
    Journal: J Org Chem; 2005 Dec 09; 70(25):10348-53. PubMed ID: 16323844.
    Abstract:
    [reaction: see text] Synthesis of (2R,3S)- or (2S,3S)-O1-acyl-3-aminoalkane-1,2-diols by ring opening of enantiopure (2R,1'S)- or (2S,1'S)-2-(1-aminoalkyl)epoxides 1 or 2, with carboxylic acids in the presence of BF3 x Et2O and chlorotrimethylsilane, is described. The conversion takes place with total selectivity and in good yield. In addition, (2R,3S)-O,O-diacyl-3-aminoalkane-1,2-diols 3 were also prepared from reaction of (2R,1'S)-2-(1-aminoalkyl)epoxides 1 with carboxylic acids under the same reaction conditions and without chlorotrimethylsilane. Mechanisms to explain both transformations are proposed.
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