ol0270428_si_001.pdf (78.93 kB)
Stereodivergent Approach to β-Hydroxy α-Amino Acids from C2-Symmetrical Alk-2-yne-1,4-diols
journal contribution
posted on 2002-11-20, 00:00 authored by Marta Amador, Xavier Ariza, Jordi Garcia, Sara SevillaA new stereodivergent route to erythro- and threo-β-substituted serines from a common C2-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 α-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.
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