%0 Journal Article %A Amador, Marta %A Ariza, Xavier %A Garcia, Jordi %A Sevilla, Sara %D 2002 %T Stereodivergent Approach to β-Hydroxy α-Amino Acids from C2-Symmetrical Alk-2-yne-1,4-diols %U https://acs.figshare.com/articles/journal_contribution/Stereodivergent_Approach_to_-Hydroxy_-Amino_Acids_from_i_C_i_sub_2_sub_-Symmetrical_Alk-2-yne-1_4-diols/3744831 %R 10.1021/ol0270428.s001 %2 https://acs.figshare.com/ndownloader/files/5838195 %K Stereodivergent %K symmetry %K C 2 %K acid %K Approach %K stereodivergent %K threo %K Hydroxy %K strategy %K olefin %K serine %K synthesis %K Stereocontrol %K hydroxyleucine %K stereochemistry %K Symmetrical %K Acid %K erythro %K Alk %K acyclic %K Stereoselective alkyne reduction %K Pd %K Amino %X A 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. %I ACS Publications