Organocatalyzed enantioselective synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylates.

Organocatalyzed enantioselective synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylates.
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DOI:
10.1016/j.tetlet.2011.10.040
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发表时间:
2011-12-14
影响因子:
1.8
通讯作者:
Zhao, Cong-Gui
Zhao, Cong-Gui
中科院分区:
化学4区
文献类型:
--
作者:
Ramireddy, Naresh;Abbaraju, Santhi;Zhao, Cong-Gui

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以双功能金鸡纳生物碱为催化剂,实现了具有生物活性的2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate衍生物的有机催化对映选择性合成。以奎宁硫脲为催化剂,1,3-环己二酮与亚烷基氰基乙酸酯衍生物进行的串联Michael加成环化反应,以较高的产率(最高可达92%)和较好的ee值(最高可达82%)得到了理想的产物。
The organocatalyzed enantioselective synthesis of biologically active 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate derivatives was achieved using bifunctional cinchona alkaloids as the catalysts. Using quinine thiourea as the catalyst, the tandem Michael addition-cyclization reaction between 1,3-cyclohexanediones and alkylidenecyanoacetate derivatives gives the desired products in high yields (up to 92%) and good ee values (up to 82%).
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