Mr. Zihao Chen


The oxetane plays an important role in medicinal and synthetic chemistry and they are isosteres of some functional groups.1 However, in comparison to epoxides, methods to synthesize oxetanes are quite limited, especially 2-substituted oxetanes because this introduces a stereocenter. Thus both the synthesis of oxetanes and the exploration of their applications in synthetic chemistry needs further exploration and study.2

To synthesize 2-acyloxetanes, we explored three methods I 3, II4 and III. These were then converted to the corresponding enolsilanes, and induced to undergo (4 + 3) cycloadditions to generate seven-membered carbocycles.5 Both types of enolsilanes reacted with good yields in intermolecular (4 + 3) cycloadditions, which underscored that oxetanes were reactive enough to participate in these ring-opening cycloadditions.



  1. Burkhard, J. A., Wuitschik, G., Rogers‐Evans, M., Müller, K., Carreira, E. M. Angew. Chem. Int. Ed, 2010, 49, 9052-9067.
  2. Bull, J. A., Croft, R. A., Davis, O. A., Doran, R., Morgan, K. F. Chem. Rev. 2016, 116, 12150-12233.
  3. Yoshimitsu, T., Arano, Y., Nagaoka, H. J. Org. Chem., 2005, 70, 2342-2345.
  4. Sabila, P. S., Howell, A. R. Tetrahedron Lett. 2007, 48, 8353–8355
  5. Yin, Z., He, Y., Chiu, P. Chem. Soc. Rev. 2018, 47, 8881-8924.

University: HKU

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