Stereodivergent approach to beta-hydroxy alpha-amino acids from C(2)-symmetrical alk-2-yne-1,4-diols.
[reaction: see text] A new stereodivergent route to erythro- and threo-beta-substituted serines from a common C(2)-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereoselective alkyne reduction to either (Z)- or (E)-olefin allows selection of the stereochemistry of alpha-carbon in the final amino acid by using a Pd(0)-catalyzed process. This strategy has been applied to the synthesis of (2S,3S)-3-hydroxyleucine.
Amador
Marta
M
Departament de Química Orgànica, Universitat de Barcelona, Martí i Franquès 1, Catalonia, Spain.
Ariza
Xavier
X
Garcia
Jordi
J
Sevilla
Sara
S
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007930:Leucine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D012694:Serine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
C470823:3-hydroxyleucine; D000596:Amino Acids; D012694:Serine; D007930:Leucine