Asymmetric Catalytic Synthesis of Hexahydropyrrolo‐isoquinolines via Three‐Component 1,3‐Dipolar‐Cycloaddition
Asymmetric Catalytic Synthesis of Hexahydropyrrolo‐isoquinolines via Three‐Component 1,3‐Dipolar‐Cycloaddition
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三组分1,3-偶极-环加成不对称催化合成六氢吡咯并异喹啉
DOI：
10.1002/chem.202102476
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Xiaoming Feng
中科院分区：
文献类型：
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作者：
Zhaojing Li;Nian Xu;Ning Guo;Yuqiao Zhou;Lili Lin;Xiaoming Feng
以手性N，N '-二氧化物-Y（OTf）3配合物为催化剂，实现了3，4-二氢异喹啉、溴乙酸酯和α，β-不饱和吡唑酰胺的不对称三组分1，3-偶极环加成反应.该方法包括碱促进原位形成二氢异喹啉叶立德，以及手性刘易斯酸催化的与α，β-不饱和吡唑酰胺的不对称[3+2]环加成。 以中等至良好的产率获得了一系列六氢吡咯并异喹啉，具有优异的非对映选择性和对映选择性。
An asymmetric three‐component 1,3‐dipolar cycloaddition of 3,4‐dihydroisoquinolines, bromoacetates and α,β‐unsaturated pyrazole amide is realized by using a chiralN,N’‐dioxide‐Y(OTf)3complex as the catalyst. The process includes a base‐promoted formation of dihydroisoquinolium ylides in situ, and a chiral Lewis acid‐catalyzed asymmetric [3+2] cycloaddition with α,β‐unsaturated pyrazole amides. A series of hexahydropyrrolo‐isoquinolines are obtained in moderate to good yields with excellent diastereo‐ and enantioselectivities.