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Diastereodivergent Formal 1,3‐Dipolar Cycloaddition of 5‐alkenyl thiazolones to Access Stereochemically Diverse Pyrrolidinyl Spirooxindoles
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2020-03-24 , DOI: 10.1002/adsc.201901541
Yu He 1, 2 , Yue Liu 2 , Yu Liu 2 , Xin‐Xin Kou 2 , Qing‐Zhu Li 2 , Jia‐Hong Li 1 , He‐Zhong Jiang 1 , Hai‐Jun Leng 2, 3 , Cheng Peng 3 , Jun‐Long Li 2
Affiliation  

We report here a stereoselective [3+2] cyclization of 5‐alkenyl thiazolones and ketimines that allows the assembly of three diastereoisomers through the combination of stereodivergent organocatalysis and the following diastereoselective transformation of products. A broad spectrum of pyrrolidinyl spirooxindoles featuring stereochemical diversity has been synthesized through organocatalytic formal 1,3‐dipolar cycloadditions with up to 98% yield, >20:1 dr and 99:1 er.

中文翻译:

5-链烯基噻唑酮的非对映异构形式1,3-偶极环加成反应可得到立体化学上不同的吡咯烷基吡咯并吲哚

我们在这里报告的5烯基噻唑酮和酮亚胺的立体选择性[3 + 2]环化,通过立体发散性有机催化和随后的产物的非对映选择性转化相结合,可以组装三种非对映异构体。通过有机催化形式的1,3-偶极环加成反应合成了具有立体化学多样性的广谱吡咯烷基螺螺辛多酯,收率高达98%,> 20:1 dr和99:1 er。
更新日期:2020-03-24
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