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Université de Montréal October 30 th 2007

Metal-Mediated Ring Formation The contribution of Paul A. Wender Guillaume Barbe Charette’s Laboratories. Université de Montréal October 30 th 2007. Paul Anthony Wender.

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Université de Montréal October 30 th 2007

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  1. Metal-Mediated Ring FormationThe contribution of Paul A. WenderGuillaume BarbeCharette’s Laboratories Université de Montréal October 30th 2007

  2. Paul Anthony Wender Born: 1947, native of Wyoming ValleyEducation1969 B. S. Wilkes CollegeMentor: Dr. William Stine1973 Ph.D. Yale UniversityAdvisor: Professor Frederick E. ZieglerCareer1974 - 1981: Harvard University 1981 – now: Stanford University

  3. Wender’s Ph.D. Work The Base-Induced Decomposition of Methyl Dialkylcyanodiazenecarboxylates. The Transformation of Ketones into Nitriles, a-carbomethoxynitriles, and a-Methylnitriles Ziegler, F. E.; Wender, P. A. J. Am. Chem. Soc.1971, 93, 4318-4319.

  4. Nickel(0)-Catalyzed Dimerization of 1,3-Butadiene Graham, C. R.; Stephenson, L. M. J. Am. Chem. Soc.1977, 99, 7098-7100.

  5. Nickel-Mediated CycloadditionIntramolecular Version – Oxidative Addition • Five-membered ring formation: cis-fused system favored• Six-membered ring formation: trans-fused system favored Graham, C. R.; Stephenson, L. M. J. Am. Chem. Soc.1977, 99, 7098-7100.

  6. Nickel-Mediated CycloadditionIntermolecular Version – Reductive Elimination Graham, C. R.; Stephenson, L. M. J. Am. Chem. Soc.1977, 99, 7098-7100.

  7. Nickel-Mediated CycloadditionIntramolecular Version – Reductive Elimination • 5-6 and 5-8 fused bicycles favored over 5-4 due to ring strain Graham, C. R.; Stephenson, L. M. J. Am. Chem. Soc.1977, 99, 7098-7100.

  8. Nickel-Mediated CycloadditionIntramolecular Version – b-Hydride Elimination • Stereochemical outcome expected to be ring-size dependent Graham, C. R.; Stephenson, L. M. J. Am. Chem. Soc.1977, 99, 7098-7100.

  9. Nickel-Mediated CycloadditionIntramolecular Version Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc.1986, 108, 4678-4679.

  10. Nickel-Mediated Cycloaddition8-membered ring formation Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc.1986, 108, 4678-4679.

  11. Nickel-Mediated Cycloaddition8-membered ring formation Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc.1986, 108, 4678-4679.

  12. Nickel-Mediated CycloadditionAsteriscanolide Total Synthesis Synthesis: 13 steps, 2.7 overall yield Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc.1988, 110, 5904-5906

  13. Nickel-Mediated CycloadditionApproach to Ophiobolin Natural Products Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarez-Subrino, A.; Vagberg, J.; Decosta, D.; Bordner, J. J. Org. Chem.1997, 62, 4908-4909.

  14. Nickel-Mediated CycloadditionStudy on Type II Reaction Wender, P. A.; Tebbe, M. J. Synthesis1991, 110, 1089-1094.

  15. Nickel-Mediated CycloadditionStudy on Type II Reaction Wender, P. A.; Tebbe, M. J. Synthesis1991, 110, 1089-1094.

  16. Nickel-Mediated CycloadditionSalsolene Oxide Total Synthesis Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron2006, 62, 7505-7511.

  17. Nickel-Mediated CycloadditionSalsolene Oxide Total Synthesis Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron2006, 62, 7505-7511.

  18. Nickel-Mediated CycloadditionSalsolene Oxide Total Synthesis Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron2006, 62, 7505-7511.

  19. Nickel-Mediated CycloadditionSalsolene Oxide Total Synthesis Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron2006, 62, 7505-7511.

  20. Nickel-Catalyzed Diels-Alder Simple alkenes do not participate in oxidative addition Alkynes reacts smoothly at room temperature Graham, C. R.; Stephenson, L. M. J. Am. Chem. Soc.1977, 99, 7098-7100.

  21. Nickel-Catalyzed Diels-AlderAlkynes Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc.1989, 111, 6432-6434.

  22. Nickel-Catalyzed Diels-AlderAlkynes Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963.

  23. Nickel-Catalyzed Diels-AlderAlkynes Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54, 1255-1275.

  24. Nickel-Catalyzed Diels-AlderAlkynes Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc.1989, 111, 6432-6434. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962-2963.

  25. Nickel-Catalyzed Diels-AlderAlkynes Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825.

  26. Nickel-Catalyzed Diels-AlderAlkynes Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825.

  27. Nickel-Catalyzed Diels-AlderAllenes Rhodium-Catalyzed Diels-AlderAllenes Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.

  28. Rhodium-Catalyzed Diels-AlderAllenes Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.

  29. Rhodium-Catalyzed Diels-AlderAllenes Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.

  30. Rhodium-Catalyzed Homo-Diels-Alder Diene-Alkyne Vinylcyclopropane-Alkyne Khusnutdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1-18.

  31. Rhodium-Catalyzed Homo-Diels-AlderAlkynes Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721.

  32. Rhodium-Catalyzed Homo-Diels-AlderAlkynes Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165.

  33. Rhodium-Catalyzed Homo-Diels-AlderAlkynes Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165.

  34. Rhodium-Catalyzed Homo-Diels-AlderAlkynes Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165.

  35. Rhodium-Catalyzed Homo-Diels-AlderAlkynes Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165.

  36. Rhodium-Catalyzed Homo-Diels-AlderAllenes Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349.

  37. Rhodium-Catalyzed Homo-Diels-AlderAlkenes Limitation Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941.

  38. Rhodium-Catalyzed Homo-Diels-AlderAllenes Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349.

  39. Rhodium-Catalyzed Homo-Diels-AlderApproach to (+)-Allocyathin B2 Wender, P. A.; Bi, F. C.; Brodney, M. A.; Gosselin, F. Org. Lett.2001, 3, 2105-2108.

  40. Rhodium-Catalyzed Homo-Diels-AlderAsymmetric Total Synthesis of Dictamnol Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett.1999, 1, 137-139.

  41. Rhodium-Catalyzed Homo-Diels-AlderAlkynes – Substituted Cyclopropanes Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443.

  42. Rhodium-Catalyzed Homo-Diels-AlderAsymmetric Total Synthesis of (+)-Aphanamol I Wender, P. A.; Zhang, L. Org. Lett.2000, 2, 2323-2326.

  43. Rhodium-Catalyzed Homo-Diels-AlderAlkynes – Substituted Cyclopropanes Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443.

  44. Rhodium-Catalyzed Homo-Diels-AlderAlkynes – Substituted Cyclopropanes Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443.

  45. Rhodium-Catalyzed Homo-Diels-AlderAlkynes – Substituted Cyclopropanes Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092.

  46. Rhodium-Catalyzed Homo-Diels-AlderAlkynes – Substituted Cyclopropanes Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089-2092.

  47. Rhodium-Catalyzed Homo-Diels-AlderAlkynes – Intermolecular Version Wender, P. A.; Rieck, H., Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977.

  48. Rhodium-Catalyzed Homo-Diels-AlderAlkynes – Intermolecular Version Wender, P. A.; Dyckman, A. J., Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611.

  49. Rhodium-Catalyzed Homo-Diels-AlderAlkynes – Intermolecular Version Wender, P. A.; Dyckman, A. J., Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611.

  50. Rhodium-Catalyzed Homo-Diels-AlderAlkynes – Intermolecular Version – Scale Up Wender, P. A.; Dyckman, A. J., Husfeld, C. O.; Scanio, M. J. C. Org. Lett. 2000, 2, 1609-1611.

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