10.1021/ol0270428.s001 Marta Amador Marta Amador Xavier Ariza Xavier Ariza Jordi Garcia Jordi Garcia Sara Sevilla Sara Sevilla Stereodivergent Approach to β-Hydroxy α-Amino Acids from <i>C</i><sub>2</sub>-Symmetrical Alk-2-yne-1,4-diols American Chemical Society 2002 Stereodivergent symmetry C 2 acid Approach stereodivergent threo Hydroxy strategy olefin serine synthesis Stereocontrol hydroxyleucine stereochemistry Symmetrical Acid erythro Alk acyclic Stereoselective alkyne reduction Pd Amino 2002-11-20 00:00:00 Journal contribution 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 A new stereodivergent route to <i>erythro</i>- and <i>threo</i>-β-substituted serines from a common <i>C</i><sub>2</sub>-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 (<i>Z</i>)- or (<i>E</i>)-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 (2<i>S</i>,3<i>S</i>)-3-hydroxyleucine.