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Enantioselective X–H insertion reactions based on carbenoids

Enantioselective X–H insertion reactions based on carbenoids. Speaker: Shaolong Zhang Supervisor: David Zhigang Wang Date: Jan. 3 nd , 2014. Outline. Background Construction of C-X bond via metal carbene N-H bond insertions O-H bond insertions S-H bond insertions

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Enantioselective X–H insertion reactions based on carbenoids

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  1. Enantioselective X–H insertion reactions based on carbenoids Speaker: Shaolong Zhang Supervisor: David Zhigang Wang Date: Jan. 3nd, 2014

  2. Outline • Background • Construction of C-X bond via metal carbene • N-H bond insertions • O-H bond insertions • S-H bond insertions • Si-H bond insertions • Application in synthesis • Summary&Acknowlegement

  3. Outline • Background • Construction of C-X bond via metal carbene • N-H bond insertions • O-H bond insertions • S-H bond insertions • Si-H bond insertions • Application in synthesis • Summary&Acknowlegement

  4. Background

  5. Background

  6. Used industrially by Meck In synthesis of (+)-Thienamycin

  7. Background

  8. General mechanistic study

  9. General points on catalysts G. Dennis *, F. Na, Chem. Soc. Rev., 2013, 42, 4918.

  10. Outline • Background • Construction of C-X bond via metal carbene • N-H bond insertions • O-H bond insertions • S-H bond insertions • Si-H bond insertions • Application in synthesis • Summary&Acknowlegement

  11. Outline • Background • Construction of C-X bond via metal carbene • N-H bond insertions • O-H bond insertions • S-H bond insertions • Si-H bond insertions • Application in synthesis • Summary&Acknowlegement

  12. N-H bond insertions

  13. N-H bond insertions

  14. N-H bond insertions

  15. Outline • Background • Construction of C-X bond via metal carbene • N-H bond insertions • O-H bond insertions • S-H bond insertions • Si-H bond insertions • Application in synthesis • Summary&Acknowlegement

  16. O-H bond insertions

  17. O-H bond insertions

  18. O-H bond insertions T. C. Maier, G. C. Fu, J. Am. Chem. Soc. 2006, 128, 4594.

  19. O-H bond insertions S. Zhu, Y. Cai, H. Mao, J. Xie, Q. Zhou, Nat. Chem. 2010, 546.

  20. O-H bond insertions

  21. Outline • Background • Construction of C-X bond via metal carbene • N-H bond insertions • O-H bond insertions • S-H bond insertions • Si-H bond insertions • Application in synthesis • Summary&Acknowlegement

  22. S-H bond insertions

  23. S-H bond insertions

  24. Outline • Background • Construction of C-X bond via metal carbene • N-H bond insertions • O-H bond insertions • S-H bond insertions • Si-H bond insertions • Application in synthesis • Summary&Acknowlegement

  25. Si-H bond insertions

  26. Si-H bond insertions

  27. Outline • Background • Construction of C-X bond via metal carbene • N-H bond insertions • O-H bond insertions • S-H bond insertions • Si-H bond insertions • Application in synthesis • Summary&Acknowlegement

  28. Application in synthesis

  29. Application in selective protein labeling

  30. Summary

  31. Thank you for your attention

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