个人简介

John Wolfe received his BA in Chemistry from the University of Colorado, Boulder, where he conducted undergraduate research in the labs of Professor Gary A. Molander. John Wolfe completed his Ph.D. in Organic Chemistry at the Massachusetts Institute of Technology under the guidance of Professor Stephen L. Buchwald. John Wolfe's thesis research was focused on metal-catalyzed C-N, C-O, and C-C bond-forming reactions of aryl halides, and involved the development of new reactions and novel catalysts. Following the completion of his Ph.D. in 1999, John Wolfe moved to the University of California, Irvine, where he conducted research as an NIH postdoctoral fellow in the labs of Professor Larry E. Overman. His postdoctoral research involved the development of new methods of synthesis of polycyclic guanidine derivatives and bicyclic ketones. Professor Wolfe joined the faculty at the University of Michigan in July, 2002. His current research is directed towards the development of new metal-catalyzed reactions for the synthesis of interesting, biologically active compounds.

研究领域

Organic Chemistry Organometallic Chemistry New Synthetic Methods Catalysis and Asymmetric Catalysis Synthesis of Natural Products

The invention of new methods, strategies, and reactions is of great importance to the progress of organic synthesis. Chemical technology and knowledge have advanced to a point where, given a sufficient amount of time, money, and manpower, it is possible to synthesize almost any organic molecule known to man. However, the synthesis of important, biologically active molecules in an efficient, practical, economical, and environmentally benign fashion still remains a great challenge to organic chemists. One way to address this challenge is to devise new means of assembling molecules by taking advantage of the unique reactivity of transition metals. To this end, our research is focused on the creation of new metal-catalyzed reactions that are applicable to the synthesis of important molecules. Research in my group involves the development of new synthetic methodology and new transition metal catalysts, asymmetric catalysis and synthesis, the study of new reaction mechanisms, and the total synthesis of natural products. Three representative areas of interest are described below. The Palladium-catalyzed stereoselective synthesis of tetrahydrofurans and Pyrrolidines. We have recently developed new palladium-catalyzed reactions of gamma-hydroxy or gamma-amino olefins with aryl and vinyl bromides that affords substituted tetrahydrofuran products. These reactions form both a carbon-carbon and a carbon-heteroatom bond in a single step, and proceed with diastereoselectivities of up to >20:1. Preliminary mechanistic studies suggest these reactions proceed through an unusual intramolecular insertion of an alkene into a Pd(Ar)(OR) or a Pd(Ar)(NRR') intermediate. These new reactions have potential applications to the stereocontrolled synthesis of a number of interesting, biologically active compounds including members of the acetogenin and the amphidinolide families of natural products . The metal-catalyzed insertion of olefins into small heterocycles. A large number of tetrahydrofuran and pyrrolidine derivatives have been shown to possess useful and interesting biological activity. One of our approaches to these compounds involves the development of a transition metal-catalyzed insertion reaction of olefins into small, strained heterocycles. This strategy would produce complex molecules in a single step from simple starting materials in a stereocontrolled manner. In addition to providing a new, useful method for organic synthesis, studies in this area will also address significant issues in organometallic chemistry. The utility of this methodology may be demonstrated in the total synthesis of several natural products including plakortone E, hyacinthacine B2, and cylindricines C and D. Tandem Wittig-Rearrangment/Aldol Reactions. We have recently discovered a new transformation that effects the coupling of O -alkyl glycolate esters with aldehydes to afford syn -1,2-diols bearing a quaternary stereocenter. These transformations proceed via an unprecedented one-pot sequential 1,2-Wittig-rearrangement/aldol reaction, and provide the products with excellent diastereoselectivity (>20:1 dr). We are currently exploring asymmetric versions of these reactions, along with applications to the synthesis of natural products such as alternaric acid and leuhistin.

近期论文

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"Enantioselective synthesis of tetrahydroquinolines, tetrahydroquinoxalines, and tetrahydroisoquinolines via Pd-Catalyzed alkene carboamination reactions" Brett A. Hopkins, John P. Wolfe, Chem. Sci. 2014,5, 4840–4844. doi: 10.1039/C4SC01327A "Synthesis of Substituted 2-Aminoimidazoles via Pd-Catalyzed Alkyne Carboamination Reactions. Application to the Synthesis of Preclathridine Natural Products" Blane P. Zavesky, Nicholas R. Babij, John P. Wolfe, Org. Lett.. 2014,16, 4952–4955. doi: 10.1021/ol502471x "Influence of Catalyst Structure and Reaction Conditions on anti- versus syn-Aminopalladation Pathways in Pd-Catalyzed Alkene Carboamination Reactions of N-Allylsulfamides" Ryan M. Fornwald, Jonathan A. Fritz, John P. Wolfe, Chem. Eur. J.. 2014, 20, 8782–8790. doi: 10.1002/chem.201402258 "Stereocontrolled Synthesis of Bicyclic Sulfamides via Pd-Catalyzed Alkene Carboamination Reactions. Control of 1,3-Asymmetric Induction by Manipulating Mechanistic Pathways" Nicholas R. Babij, Grace M. McKenna, Ryan M. Fornwald, John P. Wolfe, Org. Lett. 2014, 16, 3412–3415. doi: 10.1021/ol5015976 "Synthesis of Substituted Tetrahydroindoloisoquinoline Derivatives via Intramolecular Pd-Catalyzed Alkene Carboamination Reactions" Jeremiah Alicea, John P. Wolfe, J. Org. Chem. 2014, 79, 4212–4217. doi: 10.1021/jo500470m "Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Carboamination or Carboalkoxylation Reactions" John P. Wolfe, Top. Heterocycl. Chem. 2013, 32, 1–38. "Synthesis of Cyclic Guanidines via Pd-Catalyzed Alkene Carboamination" Blane P. Zavesky, Nicholas R. Babij, Jonathan A. Fritz, John P. Wolfe, Org. Lett. 2013,15, 5420–5423. doi: 10.1021/ol402377y "Desymmetrization of meso-2,5-Diallylpyrrolidinyl Ureas through Asymmetric Palladium-Catalyzed Carboamination: Stereocontrolled Synthesis of Bicyclic Ureas" Nicholas R. Babij, John P. Wolfe, Angew. Chem. Int. Ed. 2013,52, 9247–9250. doi: 10.1002/anie.201302720 "Synthesis of Substituted 3-Hydroxy-2-Furanone Derivatives via an Unusual Enolate Wittig Rearrangement/Alkylative Cyclization Sequence" Renata K. Everett, John P. Wolfe, Org. Lett. 2013,15, 2926-2929. doi: 10.1021/ol4009188 "Intermolecular Gold(I)-Catalyzed Alkyne Carboalkoxylation Reactions for the Multicomponent Assembly of β-Alkoxy Ketones" Danielle M. Schultz, Nicholas R. Babij, John P. Wolfe, Adv. Synth. Catal. 2012, 354, 3451-3455. doi: 10.1002/adsc.201200825 "Synthesis of Enantiomerically Enriched Imidazolidin-2-Ones through Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions" Brett A. Hopkins, John P. Wolfe, Angew. Chem. Int. Ed. 2012, 51, 9886–9890. doi: 10.1002/anie.201205233 "Asymmetric Total Synthesis of (+)-Merobatzelladine B" Nicholas R. Babij and John P. Wolfe, Angew. Chem. Int. Ed. 2012, 51, 4128-4130. doi: 10.1002/anie.201201001 "Disguise Gets a Reaction" Danielle M. Schultz and John P. Wolfe, Nature 2012,483, 42-43. doi: 10.1038/483042a "Recent Developments in Palladium-Catalyzed Alkene Aminoarylation Reactions for the Synthesis of Nitrogen Heterocycles" Danielle M. Schultz and John P. Wolfe, Synthesis 2012,44, 351-361. doi: 10.1055/s-0031-1289668 "Synthesis of Chromans via Pd-catalyzed Alkene Carboetherification Reactions" Amanda F. Ward and John P. Wolfe,Chem. Commun. 2012,48, 609-611. doi: 10.1039/C1CC15880E "Steroselective Synthesis of Substituted 1,3-Oxazolidines via Pd-Catalyzed Carboamination Reactions of O-Vinyl-1,2-Amino Alcohols " Amanda F. Ward and John P. Wolfe, Org. Lett. 2011,13, 4728-4731. doi: 10.1021/ol2020048 "Cascade Intramolecular N-Arylation/Intermolecular Carboamination Reactions for the Construction of Tricyclic Heterocycles " Georgia S. Lemen and John P. Wolfe, Org. Lett. 2011, 13, 3218-3221. doi: 10.1021/ol201123b "Intramolecular Alkene Carboamination Reactions for the Synthesis of Enantiomerically Enriched Tropane Derivatives " Danielle M. Schultz and John P. Wolfe, Org. Lett. 2011,13, 2962-2965. doi: 10.1021/ol201051q "Enantioconvergent Synthesis of (+)-Aphanorphine via Asymmetric Pd-Catalyzed Alkene Carboamination " Duy N. Mai, Brandon R. Rosen, and John P. Wolfe, Org. Lett. 2011, 13, 2932-2935. doi: 10.1021/ol2009895 "Synthesis of Saturated 1,4-Benzodiazepines via Pd-Catalyzed Carboamination Reactions" Joshua D. Neukom, Alvin S. Aquino, and John P. Wolfe, Org. Lett. 2011, 13, 2196-2199. doi: 10.1021/ol200429a