Regioselective ring opening of amino epoxides with nitriles: an easy synthesis of (2R,3S)- and (2S,3S)-1,3-diaminoalkan-2-ols with differently protected amine functions.
[reaction: see text] Transformation of enantiopure (2R,1'S)- or (2S,1'S)-2-(1-aminoalkyl)epoxides 1 or 2 into the corresponding (2R,3S)- and (2S,3S)-1,3-diaminoalkan-2-ols 3 or 4 is described. The opening of the epoxide ring with different nitriles (Ritter reaction) takes place with total selectivity and in high yields in the presence of BF3.Et2O. Interestingly, the two amine groups are differently protected. A mechanism to explain this transformation is proposed.
Concellón
José M
JM
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain. jmcg@fq.uniovi.es
Suárez
José Ramón
JR
Del Solar
Virginia
V
D000588:Amines; D004852:Epoxy Compounds; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis*; D008968:Molecular Conformation; D009570:Nitriles; D013237:Stereoisomerism
D000588:Amines; D004852:Epoxy Compounds; D017320:HIV Protease Inhibitors; D009570:Nitriles