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Stereoselective annulation between an allene, an alkene, and two nitrosoarenes to access bis(isoxazoliodine) derivatives
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2017-10-25 00:00:00 , DOI: 10.1039/c7ob02087b
Pankaj Sharma 1, 2, 3, 4 , Prakash D. Jadhav 1, 2, 3, 4 , Manisha Skaria 1, 2, 3, 4 , Rai-Shung Liu 1, 2, 3, 4
Affiliation  

This work reports metal-free annulations between one allene, two nitrosoarenes and one electron-deficient alkene to afford bis(isoxazolidine) derivatives stereoselectively. This process involves an initial formation of isoxazolidin-4-imine oxides, followed by their dipolar [3 + 2]-cycloaddition with electron-deficient alkenes. To highlight the utility, the annulations of 5-alleneyl-1-enes with nitrosoarenes were also feasible to afford the desired bis(isoxazolidine) products with excellent stereocontrol. The resulting bis(isoxazolidine) products produced from two systems were reduced with Zn/MeOH to induce reductive N–O cleavages, yielding branched polyaminols stereoselectively.

中文翻译:

丙二烯,烯烃和两个亚硝基芳烃之间的立体选择性环化反应,可制得双(异恶唑啉)衍生物

这项工作报告了一个丙二烯,两个亚硝基芳烃和一个缺电子的烯之间的无金属环化反应,可以立体选择性地生成双(异恶唑烷)衍生物。此过程涉及异恶唑烷-4-亚胺氧化物的初始形成,然后与缺电子的烯烃进行偶极[3 + 2]-环加成反应。为了突出实用性,用亚硝基芳烃环合5-亚戊基-1-烯也是可行的,以提供具有优异立体控制的所需双(异恶唑烷)产物。由两个系统产生的双(异恶唑烷)产物用Zn / MeOH还原以诱导还原性N–O裂解,从而立体选择性地产生支链聚氨基。
更新日期:2017-11-15
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