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Lewis Acid and Br Ø nst Acid Catalyzed Diazo Compounds Rearrangement

Lewis Acid and Br Ø nst Acid Catalyzed Diazo Compounds Rearrangement. 吴佩煜 2013.4.13. Contents. Introduction 1,2-H shift 1,2-aryl shift Intramolecular nucleophilic attack Ring expansion reaction Conclusion. Introduction. Introduction. Ring expansion reaction. 1,2-H shift. 1,2-H shift.

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Lewis Acid and Br Ø nst Acid Catalyzed Diazo Compounds Rearrangement

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  1. Lewis Acid and BrØnst Acid Catalyzed Diazo Compounds Rearrangement 吴佩煜 2013.4.13

  2. Contents • Introduction • 1,2-H shift • 1,2-aryl shift • Intramolecularnucleophilic attack • Ring expansion reaction • Conclusion

  3. Introduction

  4. Introduction Ring expansion reaction

  5. 1,2-H shift

  6. 1,2-H shift Roskamp, E. J. J. Org. Chem. 1989,54, 3258-3260 Feng, X. J. Am. Chem. Soc. 2010, 132, 8532–8533

  7. 1,2-H shift Maruoka, K. J. Am. Chem. Soc. 2009, 131, 11280–11281

  8. 1,2-H shift Hwang, G. and Ryu, D. H. Angew. Chem. Int. Ed. 2012, 51, 8322 –8325

  9. 1,2-H shift Kingsbury, J. S. Org. Lett., 2009, 11, 3202-3205

  10. 1,2-aryl shift

  11. 1,2-aryl shift Maruoka, K. J. Am. Chem. Soc. 2008, 130, 2434-2435

  12. 1,2-aryl shift Barluenga, J. and Valdés C. Nature Chem. 2009, 1, 494-499

  13. 1,2-aryl shift

  14. 1,2-aryl shift Carreira, E. M. Angew. Chem. Int. Ed. 2011, 50, 9085 –9088

  15. 1,2-aryl shift

  16. Intramolecularnucleophilic attack

  17. Intramolecularnucleophilic attack Maruoka, K. J. Am. Chem. Soc. 2008, 130, 14380-14381

  18. Intramolecularnucleophilic attack Akiyama, T. Org. Lett., 2009, 11, 2445-2447

  19. Intramolecularnucleophilic attack Maruoka, K. Org. Lett., 2010, 12, 1668-1671

  20. Ring expansion reaction Ring expansion reaction

  21. Ring expansion reaction Kingsbury, J. S. J. Am. Chem. Soc. 2009, 131, 878-879

  22. Ring expansion reaction Maruoka, K. J. Am. Chem. Soc. 2009, 131, 6614-6617

  23. Ring expansion reaction Kingsbury, J. S. Org. Lett., 2010, 12, 3598-3601

  24. Ring expansion reaction Maruoka, K. Chem. Commun. 2010, 46, 6810–6812

  25. Ring expansion reaction Kingsbury, J. S. Org. Lett., 2011, 13, 2004-2007

  26. Ring expansion reaction Maruoka, K. J. Am. Chem. Soc. 2011, 133, 8834-8837

  27. Ring expansion reaction Pellicciari, R. J. Org. Chem. 2011,76, 7431-7437

  28. Ring expansion reaction

  29. Ring expansion reaction Feng, X. Angew. Chem. Int. Ed. 2012, 51, 8644 –8647 Feng, X. J. Am. Chem. Soc. 2011, 133, 15268-15271

  30. Conclusion • Chemoselectivity • Regioselectivity • Stereoselective and enantioselectivity

  31. Thanks !

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