Catalytic Asymmetric 1,3-Dipolar [3+6] Cycloaddition of Azomethine Ylides with 2-Acyl Cycloheptatrienes: Efficient Construction of Bridged Heterocycles Bearing Piperidine Moiety
Catalytic Asymmetric 1,3-Dipolar [3+6] Cycloaddition of Azomethine Ylides with 2-Acyl Cycloheptatrienes: Efficient Construction of Bridged Heterocycles Bearing Piperidine Moiety
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偶氮甲碱叶立德与 2-酰基环庚三烯的催化不对称 1,3-偶极 [3 6] 环加成：有效构建带有哌啶部分的桥联杂环
DOI：
10.1021/ja503309u
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发表时间：
2014
影响因子：
15
通讯作者：
Wang Chun-Jiang
中科院分区：
文献类型：
--
作者：
Li Qing-Hua;Wei Liang;Wang Chun-Jiang
Conjugated cyclic trienes without nonbenzenoid aromatic characteristic were successfully employed as fine-tunable dipolarophiles in the Cu(I)-catalyzed asymmetric azomethine ylide-involved 1,3-dipolar [3 + 6] cycloaddition for the first time, affording a variety of bridged heterocycles bearing piperidine moiety in good yield with exclusive regioselectivity and excellent stereoselectivity. 2-Acyl group is the key factor that determines the annulation preferentially through [3 + 6]-pathway, while 2-ester group modulates the annulation through [3 + 2]-pathway.
