Synthesis of Enantiopure (αS,βS)- or (αR,βS)-β-Amino Alcohols by Complete Regioselective Opening of Aminoepoxides by Organolithium Reagents LiAlH4 or LiAlD4
journal contributionposted on 18.08.2006 by José M. Concellón, Pablo L. Bernad, Virginia del Solar, José Ramón Suárez, Santiago García-Granda, M. Rosario Díaz
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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 (αS,βS)- or (αR,βS)- 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.