New Reactions Development: Metal Catalyzed Cycloadditions
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- Wender, Paul A.; Fournogerakis, Dennis N.; Jeffreys, Matthew S.; Quiroz, Ryan V.; Inagaki, Fuyuhiko; Pfaffenbach, Magnus; "Structural Complexity Through Multicomponent Cycloaddition Cascades Enabled by Dual-Purpose, Reactivity Regenerating 1,2,3-Triene Equivalents", Nature Chemistry, 2014, 6, 448-452. Abstract, PDF.
- Paul A. Wender, Fuyuhiko Inagaki, Magnus Pfaffenbach, Matthew C. Stevens, "Propargyltrimethylsilanes as Allene Equivalents in Transition Metal Catalyzed [5+2] Cycloadditions", Organic Letters, 2014, 16(11), 2923-2925. Abstract, PDF.
- Wender, Paul A.; Lesser, Adam B.; Sirois, Lauren E.; "Rhodium Dinaphthocyclooctatetraene Complexes: Synthesis, Characterization and Catalytic Activity in [5+2] Cycloadditions", Angewandte Chemie, 2012, Published online: 1 Feb 2012. Abstract, PDF.
- Wender, Paul A.; Lesser, Adam B.; Sirois, Lauren E., "The Preparation of Cyclohelpt-4-Enones by Rhodium Catalyzed Intermolecular [5+2] Cycloaddition" Organic Syntheses, 2011, 88, 109-120. PDF.
- Wender, Paul A.; Sirois, Lauren E.; Stemmler, René T.; Williams, Travis J. "Highly Efficient, Facile, Room Temperature Intermolecular [5+2] Cyclcoadditions Catalyzed by Cationic Rhodium(I): One Step to Cycloheptenes and Their Libraries" Organic Lett., 2010, 1604-1607. Abstract, PDF,Supporting Information.
- Liu, Peng; Sirois, Lauren E.; Cheong, Paul H.-Y.; Yu, Zhi-Xiang.; Hartung, Ingo, V.; Rieck, Heiko; Wender, Paul A.; Houk, Kendall N "Electronic and Steric Control of Regioselectivities in Rh(I)-Catalyzed (5+2) Cycloadditions: Experiment and Theory" J. Am. Chem. Soc., 2010, 10127-10135.Abstract, PDF, Supporting Information.
- Paul A. Wender, René T. Stemmler, Lauren E. Sirois, "A Metal-Catalyzed Intermolecular [5+2] Cycloaddition / Nazarov Cyclization Sequence and Cascade" J. Am. Chem. Soc., 2010, 2532-2533. Abstract, PDF, Supporting Information.
- Paul A. Wender, Justin P. Christy, Adam B. Lesser, and Marc T. Gieseler, "The Synthesis of Highly-Substituted Cyclooctatetraene Scaffolds by Metal-Catalyzed [2+2+2+2] Cycloadditions: Studies on Regioselectivity, Dynamic Properties and Metal Chelation", Angewandte Chemie Int. Ed 2009, 7823-7826. Abstract, PDF, Supporting Information.
- Wender, Paul A., Strand, Daniel, “Cyclocarboamination of Alkynes with Aziridines: Synthesis of 2,3-Dihydropyrroles by a Catalyzed Formal [3+2] Cycloaddition”, JACS, 2009, 7528-7529. Abstract, PDF, Supporting Information.
- Croatt, Mitchell P.; Wender, Paul A.; "The Diene Effect: The Design, Development, and Mechaqnistic Investigation of Metal-Catalyzed Diene-yne, Diene-ene, and Diene-allene [2+2+1] Cycloaddition Reactions", Eur. J. Org. Chem., 2009, Volume 2010, Issue 1, Date: January 2010, Pages 19-32.Abstract, PDF.
- Wender, Paul; Croatt, Mitch; Kuhn, Bjorn; "Rhodium(I)-Catalyzed [2+2], [2+2+2], and [2+2+2+2] Cycloadditions of Dienes or Alkynes with a Bis-ene", Organometallic, 2009, 28(20), 5841-5844. Abstract, PDF, Supporting Information.
- Liu, P.; Cheong, P. H.; Yu, Z.-X.; Wender, P. A.; Houk, K. N. "Substituent Effects, Reactant Preorganization, and Ligand Exchange Control the Reactivity in Rh(I)-Catalyzed (5+2) Cycloadditions between Vinylcyclopropanes and Alkynes"; Angew. Chem. Int. Ed. 2008, 47, 3939-3941.Abstract, PDF, Supporting Information.
- Z.-X. Yu, P. Ha-Yeon Cheong, P. Liu, C. Legault, P. Wender, K. Houk “Origins of Differences in Reactivities of Alkenes, Alkynes, & Allenes in [Rh(CO)2Cl]2-Catalyzed (5+2) Cycloaddition Reactions with Vinylcyclopropanes” J. Am. Chem. Soc. 2008, 130, 2378-2379. Abstract, PDF,Supporting Information.
- Wender, P. A.; Christy, J. P. "Nickel(0)-Catalyzed [2 + 2 + 2 + 2] Cycloadditions of Terminal Diynes for the Synthesis of Substituted Cyclooctatetraenes" J. Am. Chem. Soc. 2007, 129, 13402-13403. Abstract, PDF, Supporting Information.
- Wender, P. A.; Paxton, T. J.; Williams, T. J.; "Cyclopentadienone Synthesis by Rhodium(I)-Catalyzed [3 + 2] Cycloaddition Reactions of Cyclopropenones and Alkynes" J. Am. Chem. Soc. 2006, 128, 14814-14815. Abstract, PDF, Supporting Information.
- Wender P. A.; Croatt, M. P.; Witulski, B. " New reactions and step economy: the total synthesis of (+/-)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4+4] cycloaddition" Tetrahedron 2006, 62, 7505-7511. Abstract, PDF.
- Wender P. A.; Deschamps, N. M.; Sun R. "Rh(I)-Catalyzed C-C Bond Activation: Seven-Membered Ring Synthesis by a [6+1] Carbonylative Ring-Expansion Reaction of Allenylcyclobutanes" Agnew. Chem. Int. Ed. 2006, 45, 3957-3960. Abstract, PDF. Supporting Information.
- Wender, P. A.; Christy, J. P. "Rhodium(I)-Catalyzed [4+2+2] Cycloadditions of 1,3-Dienes, Alkenes, and Alkynes for the Synthesis of Cyclooctadienes" J. Am. Chem. Soc. 2006, 128, 6530-6531. Abstract, PDF, Supporting Information.
- Wender, P. A.; Haustedt, L. O.; Lim, J.; Love, J. A.; Williams, T. J.; Yoon, J.-Y. "Asymmetric Catalysis of the [5 + 2] Cycloaddition Reaction of Vinylcyclopropanes and Pi-Systems" J. Am. Chem. Soc. 2006, 128, 6302-6303. Abstract, PDF, Supporting Information.
- Wender, P. A.; Croatt, M. P.; Deschamps, N. M. "Metal-Catalyzed [2+2+1] Cycloadditions of 1,3-Dienes, Allenes, and CO" Angew. Chem. Int. Ed.2006, 45, 2459-2462. Abstract, PDF, Supporting Information.
- Wender P. A.; Deschamps, N. M.; Sun R. "Rh(I)-catalyzed cleavage of unactivated C-O bonds - Carbonylative rearrangement reactions of allenyl ethers to 2-carboalkoxy-1,3-dienes" Can. J. Chem. 2005, 83, 838-842. Abstract, PDF.
- Wegner, H. A.; de Meijere, A.; Wender, P. A. "Transition Metal-catalyzed Intermolecular [5+2] and [5+2+1] Cycloadditions of Allenes and Vinylcyclopropanes" J. Am. Chem. Soc. 2005, 127, 6530-6531. Abstract, PDF, Supporting Information.
- Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Pham, S. M.; Zhang, L. "Multicomponent Cycloadditions: The Four-component [5+1+2+1] Cycloaddition of Vinylcyclopropanes, Alkynes, and CO" J. Am. Chem. Soc. 2005, 127, 2836-2837. Abstract, PDF, Supporting Information.
- Wender, P. A.; Yu, Z.; Houk, K. N. "On the Mechanism of [Rh(CO)2Cl]2 Catalyzed Intermolecular [5+2] Reactions Between Vinylcyclopropanes and Alkynes" J. Am. Chem. Soc. 2004, 126, 9154-9155. Abstract, PDF, Supporting Information.
- Wender, P. A.; Deschamps, N. M.; Williams, T. J. "Intermolecular Dienyl Pauson-Khand Reaction" Angew. Chem. Int. Ed. 2004, 43, 3076-3079.Abstract, PDF, Supporting Information.
- Wender, P. A.; Croatt, M. P.; Deschamps, N. M. "Rhodium(I)-Catalyzed [2+2+1] Cycloadditions of 1,3-Dienes, Alkenes, and CO." J. Am. Chem. Soc. 2004, 126, 5948-5949. Abstract, PDF, Supporting Information.
- Wender, P. A.; Love, J. A.; Williams, T. J. "Rhodium-Catalyzed [5+2] Cycloaddition Reactions in Water" Synlett 2003, 1295-1298. Abstract, PDF.
- Wender, P. A.; Deschamps, N. M.; Gamber, G. G. "The Dienyl Pauson-Khand Reaction" Angew. Chem. Int. Ed. 2003, 42, 1853-1857. Abstract,PDF, Supporting Information.
- Wender, P. A.; Baryza, J. L.; Brenner, S. E.; Clarke, M. O.; Gamber, G. G.; Horan, J. C.; Jessop, T. C.; Kan, C.; Pattabiraman, K.; Williams, T. J. "Inspirations from Nature. New Reactions, New Therapeutic Leads, and New Drug Delivery Systems" Pure Appl. Chem., 2003, 75, 143-156.Abstract, PDF.
- Wender, P. A.; Williams, T. J. "[(Arene)Rh(COD)]+ Complexes as Catalysts for [5+2] Cycloadditions" Angew. Chem. Int. Ed. 2002, 41, 4550-4553.Abstract, PDF, Supporting Information.
- Wender, P. A.; Pedersen, T. M.; Scanio, M. J. C. "Transition Metal-Catalyzed Hetero-[5+2] Cycloadditions of Cyclopropyl Imines and Alkynes: Hydroazepines from Simple, Readily Available Starting Materials" J. Am. Chem. Soc. 2002, 124, 15154-15155. Abstract, PDF, Supporting Information
- Wender, P. A.; Bi, F. C.; Gamber, G. G.; Gosselin, F.; Hubbard, R. D.; Scanio, M. J. C.; Sun, R.; Williams, T. J.; Zhang, L. "Toward the Ideal Synthesis. New Transition Metal-catalyzed Reactions Inspired by Novel Medicinal Leads," Pure Appl. Chem. 2002, 74, 25-31. Abstract, PDF.
- Wender, P. A.; Gamber, G. G.; Hubbard, R. D.; Zhang, L. "Three Component Cycloadditions: The First Transition Metal-Catalyzed [5+2+1] Cycloaddition Reactions" J. Am. Chem. Soc. 2002, 124, 2876-2877. Abstract, PDF, Supporting Information
- Wender, P. A.; Gamber, G. G.; Scanio, M. J. C."Serial [5+2]/[4+2] Cycloadditions: Facile, Preparative, Multi-Component Syntheses of Polycyclic Compounds From Simple, Readily Available Starting Materials" Angew. Chem. Int. Ed. 2001, 40, 3895. Abstract, PDF, Supporting Information
- Wender, P. A.; Barzilay, C. M.; Dyckman, A. J. "The First Intermolecular Transition Metal-Catalyzed [5+2] Cycloadditions with Simple, Unactivated, Vinylcyclopropanes" J. Am. Chem. Soc. 2001, 123, 179-180. PDF, Supporting Information
- Wender, P. A.; Bi, F. C.; Brodney, M. A.; Gosselin, F. "Asymmetric Synthesis of the Tricyclic Core of NGF-inducing Cyathane Diterpenes via a Transition-Metal-Catalyzed [5+2] Cycloaddition" Org. Lett. 2001, 3, 2105-2108. Abstract, PDF, Supporting Information
- Wender, P. A.; Correa, A. G.; Sato, Y; Sun, R. "Transition Metal-Catalyzed [6+2] Cycloadditions of 2-Vinylcyclobutanones and Alkenes: A New Reaction for the Synthesis of Eight-Membered Rings" J. Am. Chem. Soc. 2000, 122, 7815-7816. PDF, Supporting Information
- Wender, P. A.; Zhang L. "Asymmetric Total Synthesis of (+)-Aphanamol I Based on the Transition Metal Catalyzed [5+2] Cycloaddition of Allenes and Vinylcyclopropanes Org. Lett. 2000, 2, 2323-2326. Abstract, PDF, Supporting Information
- Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Scanio, M. J. C. "A New and Practical Five-Carbon Component for Metal-Catalyzed [5+2] Cycloadditions: Preparative Scale Syntheses of Substituted Cycloheptenones Org. Lett. 2000, 2, 1609-1611. Abstract, PDF, Supporting Information
- Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A. Rieck, H. "Transition Metal-Catalyzed [5+2] Cycloadditions with Substituted Cyclopropanes: First Studies of Regio- and Stereoselectivity" J. Am. Chem. Soc. 1999, 121, 10442-10443. PDF, Supporting Information
- Wender, P. A.; Dyckman, A. J. "Transition Metal-Catalyzed [5+2] Cycloadditions of 2-Substituted-1-Vinylcyclopropanes: Catalyst Control and Reversal of Regioselectivity" Org. Lett. 1999, 1, 2089-2092. Abstract, PDF, Supporting Information
- Wender, P. A. ; Fuji, M.; Husfeld, C. O.; Love, J. A. "Rhodium-Catalyzed [5+2] Cycloadditions of Allenes and Vinylcyclopropanes: Asymmetric Total Synthesis of (+)-Dictamnol" Org. Lett. 1999, 1, 137-139. Abstract, PDF, Supporting Information
- Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. "Transition Metal-Catalyzed [5+2] Cycloadditions of Allenes and Vinylcyclopropanes: First Studies of Endo-Exo Selectivity, Chemoselectivity, Relative Stereochemistry, and Chirality Transfer" J. Am. Chem. Soc.1999, 121, 5348-5349. PDF, Supporting Information
- Wender, P. A.; Love, J. A. "The Synthesis of Seven-Membered Rings: General Strategies and the Design and Development of a New Class of Cycloaddition Reactions" In Advances in Cycloaddition, Hermata, M. Ed.; JAI Press, Samford, CT, 1- 45, 1999.
- Wender, P. A.; Rieck, H.; Fuji, M. "The Transition Metal-Catalyzed Intermolecular [5+2] Cycloaddition: The Homologous Diels-Alder Reaction" J. Am. Chem. Soc. 1998, 120, 10976-10977. PDF, Supporting Information
- Wender, P. A.; Husfeld, C. O.; Langkopf, E; Love, J. A."First Studies of the Transition Metal-Catalyzed [5+2] Cycloadditions of Alkenes and Vinylcyclopropanes: Scope and Stereochemistry" J. Am. Chem. Soc. 1998, 120, 1940-1941. PDF, Supporting Information
- Wender, P. A.; Sperandio, D. "A New and Selective Catalyst for the [5+2] Cycloaddition of Vinylcyclopropanes and Alkynes" J. Org. Chem. 1998,63, 4164-4165. Abstract, PDF, Supporting Information
- Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss N. "The First Metal-Catalyzed Intramolecular [5+2] Cycloadditions of Vinylcyclopropanes and Alkenes: Scope, Stereochemistry, and Asymmetric Catalysis" Tetrahedron 1998, 54, 7203-7220. Abstract, PDF.
- Wender, P. A.; Smith, T. E. "Transition Metal-Catalyzed Intramolecular [4+2] Cycloadditions: Mechanistic and Synthetic Investigations" Tetrahedron1998, 54, 1255-1275. Abstract, PDF.
- Wender, P. A.; Nuss, J. M.; Smith, D. B.; Suarezsobrino, A.; Vagberg, J.; Decosta, D.; Bordner, J. "Transition Metal Catalyzed Cycloadditions: An Intramolecular [4+4] Cycloaddition Strategy for the Efficient Synthesis of Dicyclopenta[A,D]Cyclooctene 5-8-5 Ring Systems" J. Org. Chem. 1997,62, 4908-4909. PDF, Supporting Information
- Wender, P. A.; Smith, T.E. "Transition Metal-Catalyzed Intramolecular [4+2] Cycloadditions: A Novel Method for the Assembly of Nitrogen Heterocycles and Its Application to Yohimban Alkaloid Synthesis" J. Org. Chem. 1996, 61, 824-825. PDF, Supporting Information
- Wender, P. A.; Takahashi, H.; Witulski, B. "Transition-Metal-Catalyzed [5+2] Cycloadditions of Vinylcyclopropanes and Alkynes: A Homolog of the Diels-Alder Reaction for the Synthesis of 7-Membered Rings" J. Am. Chem. Soc. 1995, 117, 4720-4721. PDF, Supporting Information
- Wender, P. A.; Jenkins, T. E.; Suzuki, S. "Transition-Metal-Catalyzed Intramolecular [4+2]-Diene Allene Cycloadditions: A Convenient Synthesis of Angularly Substituted Ring-Systems With Provision for Catalyst-Controlled Chemocomplementarity and Stereocomplementarity" J. Am. Chem. Soc.1995, 117, 1843-1844. PDF
- Wender, P. A.; Smith T. E."Transition Metal-Catalyzed Intramolecular [4+2] Cycloadditions: Initial Studies on Stereochemistry and on Steroid and Vitamin-D Analog Syntheses" J. Org. Chem. 1995, 60, 2962-2963. PDF
- Wender, P. A.; Tebbe, M. J. "Nickel(0)-Catalyzed Intramolecular [4+4] Cycloadditions: 5. The Type-II Reaction in the Synthesis of Bicyclo[5.3.1]Undecadienes" Synthesis 1991, 12, 1089-1094. PDF.
- Wender, P. A.; Jenkins, T. E."Nickel-Catalyzed Intramolecular [4+2] Dienyne Cyclo-Additions: An Efficient New Method for the Synthesis of Polycycles Containing Cyclohexa-1,4-Dienes" J. Am. Chem. Soc. 1989, 111, 6432-6434. PDF
- Wender, P. A.; Ihle, N. C.; Correia C.R.D. "Nickel-Catalyzed Intramolecular [4+4] Cyclo-Additions. 4. Enantioselective Total Synthesis of (+)-Asteriscanolide" J. Am. Chem. Soc. 1988, 110, 5904-5906. PDF
- Wender, P. A.; White, A. W. "Organobis(Cuprates): A New Class of Reagents and Method for Spiroannelation" J. Am. Chem. Soc. 1988, 110, 2218-2223. PDF
- Wender, P. A.; Ihle N. C. "Nickel-Catalyzed Intramolecular [4+4] Cycloadditions: 2. Allylic Stereoinduction and Modeling Studies in the Preparation of Bicyclo[6.4.0]Dodecadienes" Tetrahedon Lett. 1987, 28, 2451-2454. Abstract, PDF.
- Wender, P. A.; Snapper, M. L. "Intramolecular Nickel Catalyzed Cycloadditions of Bis-Dienes: 3 Approaches to the Taxane Skeleton" Tetrahedon Lett. 1987, 28, 2221-2224. Abstract, PDF.
- Wender, P. A.; Ihle N. C. "Nickel-Catalyzed Intramolecular [4+4] Cycloadditions: A New Method for the Synthesis of Polycycles Containing 8-Membered Rings" J. Am. Chem. Soc. 1986, 108, 4678-4679. PDF.