Cramer, Nicolai - École polytechnique fédérale de Lausanne EPFL - Institute of Chemical Sciences and Engineering

个人简介

Dr. Nicolai Cramer was born in Stuttgart, Germany. From 1998-2003, he studied chemistry at the University of Stuttgart. He stayed at the same institution and earned his PhD degree in 2005 under the guidance of Professor Sabine Laschat. After a research stage at Osaka University, Japan, he joined the group of Professor Barry M. Trost at Stanford University as a postdoctoral fellow in 2006. From 2007 on, he worked on his habilitation at the ETH Zurich associated to the chair of Professor Erick M. Carreira and recieved the venia legendi in 2010. In fall 2010, he started as Assistant Professor at the EPF Lausanne and was promoted to Associate Professor in 2013. His main research program encompasses enantioselective metal-catalyzed transformations and their implementation for the synthesis of biologically active molecules. Education 2011 Venia Legendi for Organic Chemistry, ETH Zurich, Switzerland 2005 PhD summa cum laude, University of Stuttgart, Germany, Prof. S. Laschat 2003 ‘Diplom’ summa cum laude, University of Stuttgart, Germany, Prof. S. Laschat 19982002 Chemistry studies, University of Stuttgart, Germany Professional Experience Since 10/2015 Full Professor EPF Lausanne, Switzerland. 2013–2015 Associate Professor EPF Lausanne, Switzerland. 2010–2013 Assistant Professor EPF Lausanne, Switzerland. 2007–2010 Habilitation at the ETH Zurich, Switzerland, Prof. E. M. Carreira 2006–2007 Postdoctoral research, Stanford University, USA, Prof. B. M. Trost 3/20056/2005 Research, Osaka University, Japan, Profs. M. Murata and S. Hase 3/20019/2001 Research, CPE Lyon, France, Prof. M. A. Ciufolini

研究领域

In the broadest terms, our research interest is an amalgamation of chiral catalyst or ligand design and the development of new reaction methodology, which seeks to push frontiers of asymmetric catalysis by addressing longstanding limitations and critical problems in organic synthesis. Essentially, we aim to leverage on creative, direct and unique disconnections in important complex molecular framework, emphasizing on transition metal-catalyzed state-of-the-art C-H functionalization processes which enable asymmetric carbon-carbon and carbon-heteroatom bond forming transformations. In our ongoing quest to develop novel asymmetric transformations, a variety of transition-metal catalysts are employed such as rhodium-, palladium-, iridium-, nickel-, cobalt-, and ruthenium-complexes. In particular, we currently focus on four main robust ligand families that fit the needs of these metals and the envisaged reaction mechanisms: Chiral cyclopentadienyl (Cpx) ligands (derived from BINOL, mannitol, fulvenes); N-heterocyclic carbenes (NHC), napththyridine diamine (NDI) ligands derived from novel chiral anilines; Monodentate or bidentate phosphine-based ligands (MOP, BINAP, TADDOL-derived); 1,3,2-Diazaphospholene ligands (main group chemistry).

近期论文

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P. Laveille, P. Miéville, S. Chatterjee, E. Clerc, J.-C. Cousty, F. de Nanteuil, E. Lam, E. Mariano, A. Ramirez, U. Randrianarisoa, K. Villat, C. Copéret, N. Cramer, Chimia 2023, 77, 154-158: “Swiss Cat+, a Data-driven Infrastructure for Accelerated Catalysts Discovery and Optimization” M. D. Wodrich, R. Laplaza, N. Cramer, M. Reiher, C. Corminboeuf, Chimia 2023, 77, 139-143: “Toward in silico Catalyst Optimization” Y.-X. Cao, M. D. Wodrich, N. Cramer, ChemRxiv, DOI: 10.26434/chemrxiv-2023-5dbsv-v2: “Nickel-Catalyzed Direct Stereoselective Alpha-Allylation of Ketones with Non-conjugated Dienes” G. Zhang, N. Cramer, Angew. Chem. Int. Ed. 2023, e202301076: “Reductive Asymmetric Aza-Mislow-Evans Rearrangement by 1,3,2-Diazaphospholene Catalysis” A. Madron du Vigné, N. Cramer, Organometallics 2022, 41, 2731–2741: “Chiral Cyclic Alkyl Amino Carbene (CAAC) Transition-Metal Complexes: Synthesis, Structural Analysis, and Evaluation in Asymmetric Catalysis” O. Lahtigui, D. Forster, C. Duchemin, N. Cramer, ACS Catal. 2022, 12, 6209–6215: “Enantioselective Access to 3-Azabicyclo[3.1.0]hexanes by CpxRhIII Catalyzed C–H Activation and Cp*IrIII Transfer Hydrogenation“ M. D. Wodrich, M. Chang, S. Gallarati, Ł. Woźniak, N. Cramer, C. Corminboeuf, Chem. Eur. J. 2022, e202200399: “Mapping Catalyst-Solvent Interplay in CompetingCarboamination/Cyclopropanation Reactions” J. Klett, L. Wozniak, N. Cramer, Angew. Chem. Int. Ed. 2022, 61, e202202306: “1,3,2-Diazaphospholene-Catalyzed Reductive Cyclizations of Organohalides” J.-F. Tan, C. T. Bormann, K. Severin, N. Cramer, Chem. Sci. 2022, 13, 3409-3415: “Chemo– and regio–divergent access to fluorinated 1–alkyl and 1–acyl triazenes from alkynyl triazenes” E. Braconi, N. Cramer, Angew. Chem. Int. Ed. 2022, 61, e202112148: “Crossed Regio- and Enantioselective Iron-Catalyzed [4+2]-Cycloadditions of Unactivated Dienes” J. Mas-Rosello, N. Cramer, Chem. Eur. J. 2021, e202103683: “Catalytic reduction of oximes to hydroxylamines: current methods, challenges and opportunities” A. G. Herraiz, N. Cramer, ACS Catal. 2021, 11, 11938: “Cobalt(III)-Catalyzed Diastereo- and Enantioselective Three-Component C–H Functionalization” L. Wozniak, N. Cramer, Angew. Chem. Int. Ed. 2021, 60, 18532-18536: “Atropo-Enantioselective Oxidation-Enabled Iridium(III)-Catalyzed C–H Arylations with Aryl Boronic Esters” J.-F. Tan, C. T. Bormann, K. Severin, N. Cramer, Chem. Sci. 2021, 12, 9140-9145: “Alkynyl Triazenes Enable Divergent Syntheses of 2-Pyrones” J. Mas-Rosello, C. J. Cope, E. Tan, B. Pinson, A. Robinson, T. Smejkal, N. Cramer, Angew. Chem. Int. Ed. 2021, 60, 15524–15532 : “Iridium-Catalyzed Acid-Assisted Hydrogenation of Oximes to Hydroxylamines” J. Mas-Roselló, A. G. Herraiz, B. Audic, A. Laverny, N. Cramer, Angew. Chem. Int. Ed. 2021, 60, 13198-13244: “Chiral cyclopentadienyl ligands: design, syntheses and applications in asymmetric catalysis” K. Ozols, S. Onodera, L. Wozniak, N. Cramer, Angew. Chem. Int. Ed. 2021, 60, 655-659: “Cobalt(III)-Catalyzed Enantioselective Intermolecular Carboaminations via C-H Functionalizations” A. Laverny, N. Cramer, Organometallics 2020, 39, 4444-4456: “Accessing Monosubstituted Cyclopentadienyl Rhodium(I) andIridium(I) Complexes by a Simultaneous Nucleophilic Addition-Metalation Approach to Fulvenes” E. Braconi, A. C. Götzinger, N. Cramer, J. Am. Chem. Soc. 2020, 142, 19819-19824: “Enantioselective Iron-Catalyzed Cross-[4+4]-Cycloaddition of 1,3-Dienes Provides Chiral Cyclooctadienes” L. Wozniak, J.-F. Tan, Q.-H. Nguyen, A. Madron du Vigné, V. Smal, Y.-X. Cao, N. Cramer, Chem. Rev. 2020, 120, 10516−10543: “Catalytic Enantioselective Functionalizations of C−H Bonds by Chiral Iridium Complexes” J. H. Reed, J. Klett, C. Steven, N. Cramer, Org. Chem. Front. 2020, 7, 3521–3529: “Stay positive: catalysis with 1,3,2-diazaphospholenes” S.-G. Wang, N. Cramer, ACS Catal. 2020, 10, 8231-8236: “Asymmetric CpxRh(III)-Catalyzed Acrylic Acid C-H Functionalization with Allenes Provides Chiral γ-Lactones” B. Audic, N. Cramer, Org. Lett. 2020, 22, 5030-5034: “Rhodium(III)-Catalyzed Cyclopropane C–H/C–C Activation Sequence Provides Diastereoselective Access to α-Alkoxylated γ-Lactams” E. Braconi, N. Cramer, Angew. Chem. Int. Ed. 2020, 59, 16425-16429: “A Chiral Naphthyridine Diimine Ligand Platform Enables Nickel-Catalyzed Asymmetric Alkylidenecyclopropanations” J. Mas-Rosello, T. Smejkal, N. Cramer, Science 2020, 368, 1098-1102: “Iridium-catalyzed acid-assisted asymmetric hydrogenation of oximes to hydroxylamines” J. H. Reed, N. Cramer, ChemCatChem 2020, 12, 4262-4266: “1,3,2‐Diazaphospholenes Catalyze the Conjugate Reduction of Substituted Acrylic Acids” C. Duchemin, N. Cramer, Angew. Chem. Int. Ed. 2020, 59, 14129-14133: “Enantioselective CpxRhIII–Catalyzed Carboaminations of Acrylates” J. Diesel, N. Cramer, Chimia 2020, 74, 278-284: “Modular Chiral N-Heterocyclic Carbene Ligands for the Nickel-Catalyzed Enantioselective C–H Functionalization of Heterocycles” J.-F. Tan, C. T. Bormann, K. Severin, N. Cramer, ACS Catalysis 2020, 10, 3790-3796: “Alkynyl Triazenes as Fluoroalkyne Surrogates: Regioselective Access to 4-Fluoro-2-pyridones by a Rh(III)-Catalyzed C-H Activation-Lossen Rearrangement-Wallach Reaction” Q.-H. Nguyen, S.-M. Guo, T. Royal, O. Baudoin, N. Cramer, J. Am. Chem. Soc. 2020, 142, 2161-2167: “Intermolecular Palladium(0)-Catalyzed Atropo-enantioselective C–H Arylation of Heteroarenes” S. H. Park, S.-G. Wang, N. Cramer, ACS Catal. 2019, 9, 10226-10231: “Enantioselective Ruthenium(II)-Catalyzed Access to Benzonorcaradienes by Coupling of Oxabenzonorbornadienes and Alkynes” S.-G. Wang, Y. Liu, N. Cramer, Angew. Chem. Int. Ed. 2019, 58, 18136-18140: “Asymmetric Alkenyl C-H Functionalization by CpxRhIII forms 2H-Pyrrol-2-ones by [4+1]-Annulation of Acryl Amides and Allenes” J. Diesel, N. Cramer, ACS Catal. 2019, 9, 9164−9177: “Generation of Heteroatom Stereocenters by Enantioselective C–H Functionalization” C. Duchemin, G. Smits, N. Cramer, Organometallics 2019, 38, 3939-3947: “RhI, IrIII and CoIII Complexes with Atropchiral Biaryl Cyclopentadienyl Ligands: Syntheses, Structures and Catalytic Activities” J.-F. Tan, C. T. Bormann, F. G. Perrin, F. M. Chadwick, K. Severin, N. Cramer, J. Am. Chem. Soc. 2019, 141, 10372: “Divergent Synthesis of Densely Substituted Arenes and Pyridines via Cyclotrimerization Reactions of Alkynyl Triazenes” J. Diesel, D. Grosheva, S. Kodama, N. Cramer, Angew. Chem. Int. Ed. 2019, 58, 11044-11048: “A Bulky Chiral N-Heterocyclic Carbene Nickel Catalyst Enables Enantioselective C–H Functionalizations of Indoles and Pyrroles” J. H. Reed, P. A. Donets, S. Miaskiewicz, N. Cramer, Angew. Chem. Int. Ed. 2019, 58, 8893-8897: “A 1,3,2–Diazaphospholene–Catalyzed Reductive Claisen Rearrangement” M. Brauns, N. Cramer, Angew. Chem. Int. Ed. 2019, 58, 8902-8906: “Efficient Kinetic Resolution of Sulfur-Stereogenic Sulfoximines Exploiting CpxRhIII-Catalyzed C-H Functionalization” Ł. Woźniak, N. Cramer, Trends Chem. 2019, 1, 471-484: “Enantioselective C–H Bond Functionalizations by 3d Transition-Metal Catalysts“ D. Grosheva, N. Cramer, Chimia 2019, 73, 262-267: “Exploitation of Unconventional Electrophiles in Enantioselective Pd(0)-Catalyzed C-H Functionalizations“ K. Ozols, Y.-S. Jang, N. Cramer, J. Am. Chem. Soc. 2019, DOI:10.1021/jacs.9b02569: “Chiral Cyclopentadienyl Cobalt(III) Complexes Enable HighlyEnantioselective 3d-Metal-Catalyzed C-H Functionalizations” C. Duchemin, N. Cramer, Chem. Sci. 2019, 10, 2773–2777: “Chiral Cyclopentadienyl RhIII-Catalyzed Enantioselective Cyclopropanation of Electron-Deficient Olefins Enable Rapid Access to UPF-648 and Oxypilin Natural Products“ S.-G. Wang, N. Cramer, Angew. Chem. Int. Ed. 2019, 58, 2514–2518: “An Enantioselective CpxRh(III)–Catalyzed C–H Functionalization / Ring–Opening Route to Chiral Cyclopentenylamines” C. Duchemin, N. Cramer, Org. Chem. Front. 2019, 6, 209-212: “One-step access to N-enoxyimides by gold-catalysed addition of N-hydroxyimides to terminal alkynes” B. Audic, M. D. Wodrich, N. Cramer, Chem. Sci. 2019, 10, 781-787: “Mild complexation protocol for chiral Cpx Rh and Ir complexes suitable for in situ catalysis”