%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