Total selective synthesis of enantiopure O1-acyl-3-aminoalkane-1,2-diols by ring opening of aminoepoxides with carboxylic acids.
[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.
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
Llavona
Ricardo
R
D000605:Amino Alcohols / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000605:Amino Alcohols; D002264:Carboxylic Acids; D004852:Epoxy Compounds