Synthesis of enantiopure (alphaS,betaS)- or (alphaR,betaS)-beta-amino alcohols by complete regioselective opening of aminoepoxides by organolithium reagents LiAlH4 or LiAlD4.
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 (alphaS,betaS)- or (alphaR,betaS)- beta-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.
Concellón
José M
JM
Departamento de Química Organica e Inorganica, Facultad de Química, Universidad de Oviedo, Julian Clavería, 8, 33071 Oviedo, Spain.
Bernad
Pablo L
PL
del Solar
Virginia
V
Suárez
José Ramón
JR
García-Granda
Santiago
S
Díaz
M Rosario
MR
D000473:Alkanes / Q000737:chemistry; D017607:Aluminum Compounds / Q000737:chemistry*; D000586:Amination; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000473:Alkanes; D017607:Aluminum Compounds; D000605:Amino Alcohols; D004852:Epoxy Compounds; D018020:Lithium Compounds; C042073:lithium aluminum hydride; D003903:Deuterium