Cascade Reaction of Donor-Acceptor Cyclopropanes: Mechanistic Studies on Cycloadditions with Nitrosoarenes and cis-Diazenes
Cascade Reaction of Donor-Acceptor Cyclopropanes: Mechanistic Studies on Cycloadditions with Nitrosoarenes and cis-Diazenes
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DOI：
10.1021/acs.orglett.6b01269
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发表时间：
2016-06-17
期刊：
影响因子：
5.2
通讯作者：
Pagenkopf, Brian L.
中科院分区：
文献类型：
--
作者：
Chidley, Tristan;Vemula, Naresh;Pagenkopf, Brian L.
在Yb(OTf)(3)催化的亚硝基芳烃环加成反应中，观察到给受体环丙烷的串联开环、消环和环加成反应。该反应生成四氢-1,2-恶嗪，而不是通过原位硝基生成正常的环加合物异恶唑烷。顺式杂志也观察到类似的级联序列。对这种独特转化的机理研究为环丙烷供体-受体反应设计提供了一种全新的方法。
Tandem ring opening, elimination, and cycloaddition of donor-acceptor cyclopropanes were observed in Yb(OTf)(3)-catalyzed cycloaddition with nitrosoarenes. The reaction results in formation of tetrahydro-1,2-oxazine instead of the normal cycloadduct isoxazolidine via in situ nitrone formation. A similar cascade sequence was observed with cis-diazines. Mechanistic studies on this unique transformation offer an entirely new approach for reaction design with donor-acceptor cyclopropanes.