Ring-Strain-Driven Catalytic Carbene Formation–Cyclopropanation–Aza-Cope Rearrangement Cascade: A Facile Entry to Fused Dihydroazepines from 1,3-Dienyltriazoles
Ring-Strain-Driven Catalytic Carbene Formation–Cyclopropanation–Aza-Cope Rearrangement Cascade: A Facile Entry to Fused Dihydroazepines from 1,3-Dienyltriazoles
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DOI：
10.1055/s-0034-1379636
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发表时间：
2014-12
期刊：
影响因子：
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通讯作者：
Hua-Dong Xu;Ke-Ling Xu;Hao Zhou;Zhi‐Hong Jia;Hao Wu;Xiaodong Lu;Mei-Hua Shen
中科院分区：
文献类型：
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作者：
Hua-Dong Xu;Ke-Ling Xu;Hao Zhou;Zhi‐Hong Jia;Hao Wu;Xiaodong Lu;Mei-Hua Shen
摘要以1-磺酰基-1，3-二烯基三氮唑为起始原料，发展了一种简便合成结构独特的稠环二氢氮杂卓的方法。在环丙基环张力释放的驱动下，铑催化的α-亚氨基类卡宾形成-环丙烷化-aza-Cope重排级联反应在单一操作中有效地进行。还探讨了取代对产率和非对映选择性的影响。
Abstract A practical method for a facile entry to structurally unique ring-fused dihydroazepine has been developed using 1-sulfonyl-1,3-dienyltriazole as starting materials. Driven by ring strain release of cyclopropyl group, a rhodium-catalyzed α-imino carbenoid formation–cyclopropanation–aza-Cope rearrangement cascade takes place efficiently in a single operation. Substitution effects on yield and diastereoselectivity are also explored.