%0 Journal Article
%A Qin, Tao
%A Li, Jian-Ping
%A Xie, Ming-Sheng
%A Qu, Gui-Rong
%A Guo, Hai-Ming
%D 2018
%T Synthesis of Chiral
Acyclic Nucleosides by Sharpless
Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir
%U https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Chiral_Acyclic_Nucleosides_by_Sharpless_Asymmetric_Dihydroxylation_Access_to_Cidofovir_and_Buciclovir/7427483
%R 10.1021/acs.joc.8b02442.s001
%2 https://acs.figshare.com/ndownloader/files/13752956
%K alkenylpurine
%K Access
%K utility
%K synthesis
%K ee
%K dihydroxylation
%K side chains
%K method
%K Buciclovir
%K Synthesi
%K enantioselectivitie
%K Cidofovir
%K chiral acyclic nucleosides
%K hydroxyl groups
%K Sharpless Asymmetric Dihydroxylation
%K yield
%K Chiral Acyclic Nucleosides
%K allylpyrimidine
%X An
efficient method to construct chiral acyclic nucleosides via
Sharpless asymmetric dihydroxylation of N-allylpyrimidines
or N-alkenylpurines is reported. A range of chiral
acyclic nucleosides with two adjacent hydroxyl groups present on the
side chains could be produced in good yields (up to 97% yield) and
excellent enantioselectivities (90–99% ee). The synthetic utility
of the reaction was demonstrated by the catalytic asymmetric synthesis
of (S)-Cidofovir and (R)-Buciclovir.
%I ACS Publications