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.