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

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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 Born: 1947, native of Wyoming Valley Education 1969 B. S. Wilkes College Mentor: Dr. William Stine 1973 Ph.D. Yale University Advisor: Professor Frederick E. Ziegler Career : Harvard University 1981 – now: Stanford University

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

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

Nickel-Mediated Cycloaddition Intramolecular 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,

Nickel-Mediated Cycloaddition Intermolecular Version – Reductive Elimination Graham, C. R.; Stephenson, L. M. J. Am. Chem. Soc. 1977, 99,

Nickel-Mediated Cycloaddition Intramolecular 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,

Nickel-Mediated Cycloaddition Intramolecular Version –  -Hydride Elimination Stereochemical outcome expected to be ring-size dependent Graham, C. R.; Stephenson, L. M. J. Am. Chem. Soc. 1977, 99,

Nickel-Mediated Cycloaddition Intramolecular Version Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108,

Nickel-Mediated Cycloaddition 8-membered ring formation Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108,

Nickel-Mediated Cycloaddition 8-membered ring formation Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108,

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

Nickel-Mediated Cycloaddition Approach 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,

Nickel-Mediated Cycloaddition Study on Type II Reaction Wender, P. A.; Tebbe, M. J. Synthesis 1991, 110,

Nickel-Mediated Cycloaddition Study on Type II Reaction Wender, P. A.; Tebbe, M. J. Synthesis 1991, 110,

Nickel-Mediated Cycloaddition Salsolene Oxide Total Synthesis Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron 2006, 62,

Nickel-Mediated Cycloaddition Salsolene Oxide Total Synthesis Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron 2006, 62,

Nickel-Mediated Cycloaddition Salsolene Oxide Total Synthesis Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron 2006, 62,

Nickel-Mediated Cycloaddition Salsolene Oxide Total Synthesis Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron 2006, 62,

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

Nickel-Catalyzed Diels-Alder Alkynes Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111,

Nickel-Catalyzed Diels-Alder Alkynes Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60,

Nickel-Catalyzed Diels-Alder Alkynes Wender, P. A.; Smith, T. E. Tetrahedron 1998, 54,

Nickel-Catalyzed Diels-Alder Alkynes Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60,

Nickel-Catalyzed Diels-Alder Alkynes Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61,

Nickel-Catalyzed Diels-Alder Alkynes Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61,

Nickel-Catalyzed Diels-Alder Allenes Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, Rhodium-Catalyzed Diels-Alder Allenes

Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117,

Rhodium-Catalyzed Diels-Alder Allenes Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117,

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

Rhodium-Catalyzed Homo-Diels-Alder Alkynes Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63,

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

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

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

Rhodium-Catalyzed Homo-Diels-Alder Approach to (+)-Allocyathin B 2 Wender, P. A.; Bi, F. C.; Brodney, M. A.; Gosselin, F. Org. Lett. 2001, 3,

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

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

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

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

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

Rhodium-Catalyzed Homo-Diels-Alder Alkynes – Substituted Cyclopropanes Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes – Substituted Cyclopropanes Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1,

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

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

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

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

Rhodium-Catalyzed Homo-Diels-Alder Non-Activated Alkynes – Intermolecular Version Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123,

Rhodium-Catalyzed Homo-Diels-Alder Non-Activated Alkynes – Intermolecular Version Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. J. Am. Chem. Soc. 2001, 123,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes – Intermolecular Version Wender, P. A.; Pedersen, T. M., Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes – Intermolecular Version Wender, P. A.; Pedersen, T. M., Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes – Intermolecular Version Wender, P. A.; Pedersen, T. M., Scanio, M. J. C. J. Am. Chem. Soc. 2002, 124,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes – Intermolecular Version Wegner, H. A.; de Meijer, A.; Wender, P. A. J. Am. Chem. Soc. 2005, 127,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes – Intermolecular Version Wegner, H. A.; de Meijer, A.; Wender, P. A. J. Am. Chem. Soc. 2005, 127,

Rhodium-Catalyzed Homo-Diels-Alder Alkynes – Intermolecular Version Wegner, H. A.; de Meijer, A.; Wender, P. A. J. Am. Chem. Soc. 2005, 127,

Rhodium-Catalyzed Cyclisation Diene + Alkene + Alkyne

Rhodium-Catalyzed [4+2+2] Wender, P. A.; Christy, J. P. J. Am. Chem. Soc. 2006, 128,

Rhodium-Catalyzed [4+2+2] Wender, P. A.; Christy, J. P. J. Am. Chem. Soc. 2006, 128,

Rhodium-Catalyzed Cyclisation Diene + Alkene + CO

Rhodium-Catalyzed Pauson-Khand Diene + alkene : Intramolecular Version Wender, P. A.; Croatt, M. P., Deschamps, N. M. J. Am. Chem. Soc. 2004, 126,

Rhodium-Catalyzed Pauson-Khand Diene + allene : Intramolecular Version Wender, P. A.; Croatt, M. P., Deschamps, N. M. Angew. Chem. Int. Ed. 2006, 45,

Rhodium-Catalyzed Cyclisation Diene + Alkyne + CO

Rhodium-Catalyzed Pauson-Khand Diene + alkyne : Intramolecular Version Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem. Int. Ed. 2003, 42,

Rhodium-Catalyzed Pauson-Khand Diene + alkyne : Intramolecular Version Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem. Int. Ed. 2003, 42,

Rhodium-Catalyzed Pauson-Khand Diene + alkyne : Intramolecular Version Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem. Int. Ed. 2003, 42,

Rhodium-Catalyzed Cyclisation Alkynes – Intermolecular Version – CO insertion Wender, P. A.; Gamber, G. G., Hubbard, R. D.; Zhang, L. J. Am. Chem. Soc. 2002, 124,

Rhodium-Catalyzed Cyclisation VCP + Alkyne + CO

Rhodium-Catalyzed Cyclisation VCP + Alkene + CO

Rhodium-Catalyzed Homo-Diels-Alder Alkenes + CO Wang, Y.; Wang, J.; Su, J.; Huang, F.; Jiao, L.; Liang, Y.; Yang, D.; Zhang, S.; Wender, P. A.; Yu, Z. J. Am. Chem. Soc. 2007, 129,

Rhodium-Catalyzed Homo-Diels-Alder Alkenes + CO Wang, Y.; Wang, J.; Su, J.; Huang, F.; Jiao, L.; Liang, Y.; Yang, D.; Zhang, S.; Wender, P. A.; Yu, Z. J. Am. Chem. Soc. 2007, 129,

Rhodium-Catalyzed Cyclisation Vinylcyclobutanone + Alkene/allene

Wender, P. A.; Correa, A. G., Sato, Y.; Sun, R. J. Am. Chem. Soc. 2000, 122,

Rhodium-Catalyzed [4+2+2] Wender, P. A.; Paxton, T. J.; Williams, T. J. J. Am. Chem. Soc. 2006, 128,

Rhodium-Catalyzed [4+2+2] Wender, P. A.; Paxton, T. J.; Williams, T. J. J. Am. Chem. Soc. 2006, 128,

Rhodium-Catalyzed Cyclisation New Catalysts Gomez, F. J.; Kamber, N. E.; Deschamps, N. M.; Cole, A. P.; Wender, P. A.; Waymouth, R. M. Organometallics 2007, 26,

Rhodium-Catalyzed Cyclisation New Catalysts Gomez, F. J.; Kamber, N. E.; Deschamps, N. M.; Cole, A. P.; Wender, P. A.; Waymouth, R. M. Organometallics 2007, 26,

Rhodium-Catalyzed Cyclisation New Catalysts Wender, P. A.; Williams, T. J. Angew. Chem. Int. Ed. 2002, 41,