秦婷, 陈平平, 李淼, 陈治明. C2轴手性双硫脲催化不对称Sulfa-Michael/Aldol串联反应[J]. 云南大学学报(自然科学版), 2020, 42(2): 345-351. doi: 10.7540/j.ynu.20190620
引用本文: 秦婷, 陈平平, 李淼, 陈治明. C2轴手性双硫脲催化不对称Sulfa-Michael/Aldol串联反应[J]. 云南大学学报(自然科学版), 2020, 42(2): 345-351. doi: 10.7540/j.ynu.20190620
QIN Ting, CHEN Ping-ping, LI Miao, CHEN Zhi-ming. Asymmetric Sulfa-Michael/Aldol tandem reaction catalyzed by C2 axis chiral thiourea[J]. Journal of Yunnan University: Natural Sciences Edition, 2020, 42(2): 345-351. DOI: 10.7540/j.ynu.20190620
Citation: QIN Ting, CHEN Ping-ping, LI Miao, CHEN Zhi-ming. Asymmetric Sulfa-Michael/Aldol tandem reaction catalyzed by C2 axis chiral thiourea[J]. Journal of Yunnan University: Natural Sciences Edition, 2020, 42(2): 345-351. DOI: 10.7540/j.ynu.20190620

C2轴手性双硫脲催化不对称Sulfa-Michael/Aldol串联反应

Asymmetric Sulfa-Michael/Aldol tandem reaction catalyzed by C2 axis chiral thiourea

  • 摘要: 合成了3种基于联芳基轴手性骨架的多氢键、多手性中心、结构对称可调的双硫脲催化剂 1a~1c ,并将其用于催化Sulfa-Michael/Aldol串联反应合成噻吩类衍生物. 研究表明:在室温(25 ℃)下,THF作为溶剂,催化剂 1c 的用量为摩尔分数20%. Sulfa-Michael/Aldol串联反应取得了较高的收率(79%~95%)和较高的对映选择性(86%~95%)和非对映选择性(>92∶8)

     

    Abstract: Three kinds of dithiourea catalysts 1a1c with multi-hydrogen bond and multi-chiral center structure based on biaryl axis chiral skeleton were synthesized and used to catalyze the synthesis of thiophene derivatives by Sulfa-Michael/Aldol series reaction. The conditions of the reaction were optimized. Studies have shown that at room temperature (25 °C), THF as a solvent, the amount of catalyst 1c is 20 mol%, Sulfa-Michael/Aldol series reaction achieved higher yield (79%—95%) and higher enantioselectivity (86%—95%) and diastereoselectivity (>92∶8dr).

     

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