Synthesis of Chiral Acyclic Pyrimidine Nucleosides with a Sulfur-Containing Side Chain via Enantioselective Tandem Conjugate Addition/Protonation,Asian Journal of Organic Chemistry

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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 2.8 ) Pub Date : 2017-11-22 03:00:29 , 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

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AdPro: A direct route to chiral pyrimidine acyclic nucleoside analogues with a sulfur-containing side chain has been 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 were formed in excellent yields (95–99 %) and moderate to excellent enantioselectivities (up to 99 % ee).

中文翻译：

通过对映选择性串联共轭加成/质子合成具有硫侧链的手性无环嘧啶核苷。

AdPro：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成/质子化反应，已经报道了具有含硫侧链的手性嘧啶无环核苷类似物的直接途径。在奎宁衍生的硫脲催化剂的存在下，形成了多种手性含硫嘧啶无环核苷类似物，收率极高（95–99％），对映选择性中等（至99％ee）。

更新日期：2017-11-22

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