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Synthesis of Chiral Acyclic Pyrimidine Nucleosides with a Sulfur‐Containing Side Chain via Enantioselective Tandem Conjugate Addition/Protonation
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2017-11-22 , DOI: 10.1002/ajoc.201700533
Jian-Ping Li 1 , Hao-Ran Tuo 1 , Ming-Sheng Xie 1 , Bo Kang 1 , Gui-Rong Qu 1 , Hai-Ming Guo 1
Affiliation  

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).

中文翻译:

通过对映选择性串联共轭加成/质子合成具有含硫侧链的手性无环嘧啶核苷。

据报道,通过硫代乙酸与α-嘧啶取代的丙烯酸酯的对映选择性串联共轭加质子化反应,可以直接制得具有含硫侧链的手性嘧啶无环核苷类似物。在存在奎宁衍生的硫脲催化剂的情况下,可以获得多种手性含硫嘧啶无环核苷类似物,收率极高(95-99%),对映选择性值中等至极好(ee高达99%)。
更新日期:2017-11-22
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