Ring opening of chiral 2-(1-aminoalkyl)epoxides by aliphatic thiols with total selectivity: synthesis of enantiopure 3-amino-1-(alkylthio)alkan-2-ols |
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| Authors: | José M Concellón Virginia del Solar José Ramón Suárez Elena G Blanco |
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| Institution: | Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julían Clavería, 8, 33071 Oviedo, Asturias, Spain |
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| Abstract: | We have studied the thiolysis of (2R,1′S)- or (2S,1′S)-2-(1-aminoalkyl)epoxides 1 or 2 in the presence of BF3·OEt2. The ring opening took place at C-3 with complete regioselectivity, affording the corresponding enantiopure (2R,3S)- or (2S,3S)-3-amino-1-(alkylthio)alkan-2-ols 3 or 4 in good or high yield. The structures of compounds 3 and 4 have been proposed based on HMBC NMR experiments. |
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