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Investigation and Synthetic Utility of Base-Promoted Irreversible Cyclization: A Transition-Metal-Free Approach

This report highlights the investigation and synthetic utility of base-promoted irreversible cyclization, a transition-metal-free approach for the synthesis of valuable intermediates and biologically active compounds. The critical role of the base, the mechanism involving highly reactive isocyanate, and the redox-neutral nature of this reaction are discussed. Further reading on the topic is also provided.

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Investigation and Synthetic Utility of Base-Promoted Irreversible Cyclization: A Transition-Metal-Free Approach

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  1. Group Meeting Report Reporter: Man Li Supervisor: Prof. Mo Date: 2016-09-02

  2. Introduction D.-G. Yu et al., Angew.Chem. Int. Ed.,2016, 55, 7068-7072

  3. Introduction D.-G. Yu et al., Angew.Chem. Int. Ed.,2016, 55, 7068-7072

  4. Introduction H. Alper et al., Org. Lett.,2013, 15, 1998 Q. Zhu et al., Chem. Commmun., 2013, 49, 173 S.-C. Chuang et al., Org. Lett., 2013, 15, 1468 Y. Zhang et al., Tetrahedron, 2013, 69, 6519

  5. Investigation

  6. Investigation

  7. Investigation

  8. Investigation

  9. Investigation

  10. Investigation (13b) N. Nama et al., RSC Adv.,2015, 5, 78374 (6c) D. W. End et al., Eur. J. Org. Chem., 2004, 479

  11. Investigation (6a) H. Uno et al., Chem. Pharm. Bull., 1980, 28, 2618 (6b) N. Dereu et al., J. Med. Chem., 1992, 35, 4306

  12. Investigation

  13. Investigation C. Yang et al., Bio. Med. Chem., 2013, 21, 2960

  14. Conclusion • The critical role of the base (excess of base). • Synthetic utility (synthesis of some valuable intermediates and biologically active compounds). • Transition-metal-free and redox-neutral. • Mechanism (highly reactive isocyanate). • Irreversible cyclization (promoting the equilibrium).

  15. Further reading C.-J. Xi et al., J. Org. Chem., 2016, 81, 6672-6676

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