Stereoselective annulation between an allene, an alkene, and two nitrosoarenes to access bis(isoxazoliodine)
Pankaj Sharma1, Prakash D Jadhav, Manisha Skaria
1Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, 30013, Republic of China. rsliu@mx.nthu.edu.tw.
Abstract:
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.
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