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Synthesis of Chiral Acyclic Pyrimidine Nucleosides with a Sulfur‐Containing Side Chain via Enantioselective Tandem Conjugate Addition/Protonation
Author(s) -
Li JianPing,
Tuo HaoRan,
Xie MingSheng,
Kang Bo,
Qu GuiRong,
Guo HaiMing
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700533
Subject(s) - chemistry , enantioselective synthesis , pyrimidine , protonation , conjugate , nucleoside , thiourea , tandem , combinatorial chemistry , stereochemistry , catalysis , side chain , organic chemistry , ion , mathematical analysis , polymer , mathematics , materials science , composite material
A direct route to chiral pyrimidine acyclic nucleoside analogues with a sulfur‐containing side chain is reported via enantioselective tandem conjugated addition‐protonation reactions of thioacetic acid to α‐pyrimidine substituted acrylates. In the presence of a quinine‐derived thiourea catalyst, diverse chiral sulfur‐containing pyrimidine acyclic nucleoside analogues could be obtained in excellent yields (95–99 %) and with moderate to excellent enantioselectivity values (up to 99 % ee ).
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