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Synthesis of Enantiopure (αSS)- or (αRS)-β-Amino Alcohols by Complete Regioselective Opening of Aminoepoxides by Organolithium Reagents LiAlH4 or LiAlD4

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journal contribution
posted on 18.08.2006 by José M. Concellón, Pablo L. Bernad, Virginia del Solar, José Ramón Suárez, Santiago García-Granda, M. Rosario Díaz
The reaction of chiral (2R,1‘S)- or (2S,1‘S)-2-(1-aminoalkyl)epoxides, 1 or 2 with a variety of organolithium compounds to obtain the corresponding (αSS)- or (αRS)- β-amino alcohols in enantiopure form is reported. In both cases, the opening of the oxirane ring at C-3 proceeded with total regioselectivity. Moreover, the ring opening of aminoepoxides 1 or 2 by hydride (utilizing LiAlH4) to obtain the corresponding (2S,3S)- or (2R,3S)-3-aminoalkan-2-ols is also described. The reaction of 1 or 2 with LiAlD4 in place of LiAlH4 gave the corresponding (2S,3S)- or (2R,3S)-3-amino-1-deuterioalkan-2-ols.