New Methods of Indole Formations and Applications in Total Synthesis
|
|
|
- Ethel Little
- 6 years ago
- Views:
Transcription
1 ew Methods of Indole Formations and Applications in Total Synthesis Palladium-Catalyzed Synthesis of 2-(Aminomethyl)indoles from Ethyl 3-(o-Trifluoroacetamidophenyl)-1-Propargyl Carbonate Ilaria Ambrogio, Sandro Cacchi and Giancario Fabrizi Org. Lett., 2006, ASAP and A ew Modular Indole Synthesis. Construction of the Highly Strained CDEF Parent Tetracycle of odulisporic Acids A and B Amos B. Smith, III, László Kürti and Akin H. Davulcu Org. Lett., 2006, ASAP Erick B. Iezzi, PhD Current Literature May 6, 2006 Erick Wipf Group 1 5/10/2006
2 Why are these articles significant? ew routes to functionalized indoles: - significant for natural product and pharmaceutical drug synthesis Cacchi s group developed a simple approach to 2-(aminomethyl)indoles and the important class of 2-(piperazin-1-ylmethyl)indoles Smith s group developed a new synthesis of tetracyclic indoles via a Stille crosscoupling/buckwald-hartwig union/cyclization Erick Wipf Group 2 5/10/2006
3 Synthesis and Functionalization of Indoles Classical methods (over last 100 years): - Fisher synthesis - Gassman synthesis - Madelung cyclization - Bischler synthesis O Br + Bischler-Möhlau synthesis H 2 heat H Palladium-catalyzed syntheses (over last 40 years): - industrial synthesis of acetaldehyde from ethylene (PdCl 2 and CuCl 2 ) launched a new area of research - fewer steps, less waste, etc. Erick Wipf Group 3 5/10/2006
4 Alkyne-Based Palladium-Catalyzed Assembly of Indoles Mechanism Example Cacchi and Fabriz. Chem. Rev. 2005, 105, 2873 Erick Wipf Group 4 5/10/2006
5 Alkene-Based Palladium-Catalyzed Assembly of Indoles Mechanism Example Cacchi and Fabriz. Chem. Rev. 2005, 105, 2873 Erick Wipf Group 5 5/10/2006
6 Palladium-catalyzed hydroarylation/cyclization of alkynes (Cacchi s methodology) Used to construct heterocyclic rings: - butenolides - quinolines - chromenes - coumarins - chromanols OEt I OMe OMe TsOH (10%), EtOH/H 2 O (8:2), 2 h, rt, 87% OMe OTHP OEt Pd(OAc) 2 (5 mol%), DMF, KOOCH, 40 o C, 4 h, 66% OEt OEt OTHP CHO OTHP TsOH (10%), Me 2 CO/H 2 O (8:2), 24 h, rt, 86% O OH H OMe CrO 3, Me 2 CO/HCl 2 (8:2), 2.5 h, rt, 79% O O OMe Cacchi, et al. Synlett. 1997, 1367 Erick Wipf Group 6 5/10/2006
7 Palladium-Catalyzed Synthesis of 2-(Aminomethyl)indoles (Cacchi et al., ASAP) desired product * A new palladium-catalyzed cyclization of an acyclic alkyne to a free -H functionalized indole! interesting result Erick Wipf Group 7 5/10/2006
8 Synthesis of 2-(piperazin-1-ylmethyl)indoles (Cacchi et al., ASAP) 2 privileged structures (indole and piperazine nuclei) - significant components in pharmaceutical chemistry (i.e., Clozapine) - formed in a single step Two C- bonds formed in a single operation Stepwise pathways (2 & 3 positions) H Ph Ph Cl H Ar H aq. CH 2 O, CH 2 Cl 2 / AcOH (4:1), rt, 30 min. 50% H H R 2 H, DMF, 60 o C H Ar Gmeiner, et al. J. Med. Chem. 2000, 43, 4563 Erick Wipf Group 8 5/10/2006
9 Synthesis of Starting Materials and Evaluation of Conditions for 2-(Piperazin-1-ylmethyl)indole Formation I O O TFAA, THF, Et 3, 0 o C, 2 h O O p-tsoh, 40 o C, Acetone/H 2 O (1:1), 6 h H 2 PdCl 2 (PPh 3 ) 2, CuI, Et 2 H, DMF, 60 o C 12 h HCOCF 3 Ethyl chloroformate, CH 2 Cl 2, Et 3, 0 o C, 2 h 80% (4 steps) HCOCF 3 OCO 2 Et Erick Wipf Group 9 5/10/2006
10 Evaluation of Functional Groups in 2-(Piperazin-1-ylmethyl)indole Formations Erick Wipf Group 10 5/10/2006
11 Evaluation of Secondary Amines and Proposed Reaction Mechanism HCOCF 3 OCO 2 Et Amine, Pd cat. H or H R 2 X = C,O X Proposed mechanism ot acidic enough Erick Wipf Group 11 5/10/2006
12 A ew Modular Indole Synthesis. Construction of the Highly Strained CDEF Parent Tetracycle of odulisporic Acids A & B (Smith et al., ASAP) odulisporanes: - a novel class of indole diterpene alkaloids - display potent insecticidal properties (i.e., fleas and ticks) - modulation of the invertebrate-specific glutamate-gated chloride ion channels - odulisporic acid A first reported by Merck in 1997 as a lead compound (potentcy, stability and pharmacokinetic profile was not optimal!) Erick Wipf Group 12 5/10/2006
13 Attempts to Synthesize the CDE Core via Known Indole Formations (Smith et al., ASAP) Reported approaches to CDE tricycle Application of the Fisher Indole Synthesis High strain in five-membered system! Erick Wipf Group 13 5/10/2006
14 Stille Cross-Coupling/Buchwald-Hartwig Union/Cyclization Tactic (Smith et al., ASAP) o reaction with 2.5 mol% cat. Erick Wipf Group 14 5/10/2006
15 Preparation of a Highly Substituted and Strained Indole Derived from (+)-Estrone and Construction of Diverse Indoles Erick Wipf Group 15 5/10/2006
16 Summary of ew Indole Methodologies Cacchi s group developed a simple approach to 2-(aminomethyl)indoles and 2-(piperazin-1-ylmethyl)indoles under mild conditions in a single operation - high product yields - application to functionalized indoles Smith s group developed a new indole synthesis via a Stille/Hartwig-Buchwald coupling using mild conditions - application to structurally diverse indoles, especially novel tricyclic systems Erick Wipf Group 16 5/10/2006
Arylhalide-Tolerated Electrophilic Amination of Arylboronic Acids with N-Chloroamides Catalyzed by CuCl at Room Temperature
Current Literature July 19, 08 Jitendra Mishra Arylhalide-Tolerated Electrophilic Amination of Arylboronic Acids with -Chloroamides Catalyzed by CuCl at Room Temperature Aiwen Lei et.al. College of the
Direct Oxidative Heck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans
Direct xidative eck Cyclizations: Intramolecular Fujiwara-Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans by Zhang,.; Ferreira, E. M.; Stoltz, B. M. Angewandte
Rising Novel Organic Synthesis
Literature report Rising Novel Organic Synthesis Methods Based on the Cleavage of N-N and N-O Bonds Reporter: Zhang-Pei Chen Checker : Mu-Wang Chen Date: 04/03/2014 Kürti, L. et al. Kürti, L. et al. Science
Microwave-promoted synthesis in water
Microwave-promoted synthesis in water icholas E. Leadbeater nicholas.leadbeater@uconn.edu Outline of what we do Synthesis / Methodology / ew techniques Pure organic synthesis eg. Baylis-Hillman eaction
Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides
Negishi Coupling of Secondary Alkylzinc alides with Aryl Bromides and Chlorides X X = Br, Cl 2 1 ZnBr 1, 2 = Alkyl Cat. Pd(OAc) 2 Ligand TF/Toluene rt or 60 o C 1 2 J. Am. Chem. Soc. 2009, ASAP Article
Palladium-Mediated Functionalization of Heteroaromatic Cations: Comparative Study on Quinolizinium Cations
Palladium-Mediated Functionalization of Heteroaromatic Cations: Comparative Study on Quinolizinium Cations Domingo Garcia-Cuadrado, Ana M. Cuadro, Bernado M. Barchin, Ana unez, Tatiana Caneque, Julio Alvarez-
Additions to Metal-Alkene and -Alkyne Complexes
Additions to tal-alkene and -Alkyne Complexes ecal that alkenes, alkynes and other π-systems can be excellent ligands for transition metals. As a consequence of this binding, the nature of the π-system
Supporting Information
Supporting Information An efficient and general method for the Heck and Buchwald- Hartwig coupling reactions of aryl chlorides Dong-Hwan Lee, Abu Taher, Shahin Hossain and Myung-Jong Jin* Department of
Indoles from Simple Anilines and Alkynes: Palladium-Catalyzed C-H Activation Using Dioxygen as the Oxidant
Indoles from Simple Anilines and Alkynes: Palladium-Catalyzed C- Activation Using Dioxygen as the xidant Zhuangzhi Shi, Chun Zhang, Si Li, Delin Pan, Shengtao Ding, Yuxin Cui, and ing Jiao Angew. Chem.
Recent advances in transition metal-catalyzed or -mediated cyclization of 2,3-allenoic acids: New methodologies for the synthesis of butenolides*
Pure Appl. Chem., Vol. 76, No. 3, pp. 651 656, 2004. 2004 IUPAC Recent advances in transition metal-catalyzed or -mediated cyclization of 2,3-allenoic acids: New methodologies for the synthesis of butenolides*
C H Activated Trifluoromethylation
Literature report C H Activated Trifluoromethylation Reporter:Yan Fang Superior:Prof. Yong Huang Jun. 17 th 2013 Contents Background Trifluoromethylation of sp-hybridized C-H Bonds Trifluoromethylation
Nine-Step Enantioselective Total Synthesis of (+)-Minfiensine
ine-step nantioselective Total Synthesis of (+)-Minfiensine Jones, S. B.; Simmons, B.; MacMillan, D. W. C.* J. Am. Chem. Soc. 2009, ASAP. DI: 10.1021/ja906472m Kara George Wipf Group - Current Literature
Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group.
Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group. akatani, Y.; Koizumi, Y.; Yamasaki, R.; Saito, S. rg. Lett. 2008, 10, 2067-2070. An Annulation Reaction for the Synthesis
Larock Indole synthesis
Larock ndole synthesis CE 676 ilamber Mate 12/08/2016 Dr. Totah Discovery and development Utility and scope The reaction Advantages and limitations Application 2 ndole Discovery Benzene ring Pyrrole ring
Supporting Information for
Supporting Information for Room Temperature Palladium-Catalyzed Arylation of Indoles icholas R. Deprez, Dipannita Kalyani, Andrew Krause, and Melanie S. Sanford* University of Michigan Department of Chemistry,
Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from N-tert- Butanesulfinyl Aldimines
Asymmetric Copper-Catalyzed Synthesis of α-amino Boronate Esters from -tert- Butanesulfinyl Aldimines R BR 2 J. Am. Chem. Soc. 2008, 130, 6910. Melissa A. Beenen, Chihul An, and Jonathan A. Ellman rrent
Short Access to (+)-Lupinine and (+)-Epiquinamide via Double Hydroformylation
Short Access to (+)-Lupinine and (+)-Epiquinamide via Double Hydroformylation Kai Gao Checker: Changbin Yu Mann, A.* et al rg. Lett. 2009, ASAP Strategy for the formation of quinolizidine alkaloids R H
Organic Tutorials 3 rd Year Michaelmas Transition Metals in Organic Synthesis: (General paper level) ! 1! Reading
rganic Tutorials 3 rd Year Michaelmas 2010 Transition Metals in rganic Synthesis: (General paper level) Reading 1. Lecture Course, and suggested references from this. 2. Clayden, Greaves, Warren and Wothers.
Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides
Chapter 10. Reactions of Alcohols, Amines, Ethers, and Epoxides Learning objectives: 1. Provide both IUPAC and common (when applicable) names for alcohols and ethers. 2. Describe the physical properties
Rhenium-Catalyzed Synthesis of Multisubstituted Aromatic Compounds via C-C Single-Bond Cleavage
henium-catalyzed Synthesis of Multisubstituted Aromatic Compounds via C-C Single-Bond Cleavage Kuninobu, Y.; Takata,.; Kawata, A.; Takai, K. rg. Lett. ASAP Et 5 6 cat. [ebr(c) 3 (thf)] 2 5 6 Current Literature
A New Strategy for Efficient Synthesis of Medium and Large Ring Lactones without High Dilution or Slow Addition
A ew Strategy for Efficient Synthesis of Medium and Large ing Lactones without High Dilution or Slow Addition BF 3 Et 2 TIPS 2,4,6-collidine n + n+2 ' ' Zhao, W.; Li, Z; Sun, J. J. Am. Chem. Soc. 2013
Total Synthesis of (+)-Suaveolindole
1 Total Synthesis of (+)-Suaveolindole 15 2 C 16 11 Emile J. Velthuisen and Samuel J. Danishefsky J. Am. Chem. Soc. 2007, 9, 10640-10641 Julia Vargas September 15, 2007 2 utline Isolation and Elucidation
Construction of C-C or C-N Bond via C-H Activation ~Chemistry of Yong-Qiang Tu~
Literature Seminar 2010.5.26 Yao u(2) Construction of C-C or C-N Bond via C-H Activation ~Chemistry of Yong-Qiang Tu~ Contents: 1. Yong-Qiang Tu's Profile 2.LatestWorkofProfessorTu 2-1. C-H Activation
Filip Petronijevic Current Literature Presentation April, 24 th 2010.
Filip Petronijevic Current Literature Presentation April, 24 th 2010. Total Synthesis of ()-mplanadine A Using an Iridium-Catalyzed Pyridine C- Functionalization Daniel F. Fischer and Richmond Sarpong
ASYMMETRIC PALLADIUM-CATALYZED ALKENE CARBOAMINATION REACTIONS FOR THE SYNTHESIS OF CYCLIC SULFAMIDES
AYMMETIC PALLADIUM-CATALYZED ALKEE CABAMIATI EACTI F TE YTEI F CYCLIC ULFAMIDE Chem. Eur. J. 2016, 22, 5919 5922 Zachary J. Garlets, Kaia. Parenti, and John P. Wolfe James Johnson Wipf Group Current Literature
Literature Report 3. Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A. Date :
Literature Report 3 Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A Reporter : Xiao-Yong Zhai Checker : Shubo u Date : 2017-10-30 Pritchett, B. P.; Donckele, E. J.; Stoltz, B. M. Angew.
Suggested solutions for Chapter 40
s for Chapter 40 40 PBLEM 1 Suggest mechanisms for these reactions, explaining the role of palladium in the first step. Ac Et Et BS () 4 2 1. 2. K 2 C 3 evision of enol ethers and bromination, the Wittig
Literature Report IX. Cho, S. H. et al. Org. Lett. 2016, 18, Cho, S. H. et al. Angew. Chem. Int. Ed. 2017, 56,
Literature Report IX ynthesis of β-aminoboronates by Copper(I)- Catalyzed Addition of Diborylalkanes to Imines Reporter Checker Date : hubo Hu : Xiaoyong Zhai : 2017-9-1818 Cho,. H. et al. rg. Lett. 2016,
Steric and Electronic Controllers in Ring-Closing Metathesis Reactions. Jennifer E. Farrugia October 29, 2003
Steric and Electronic Controllers in Ring-Closing Metathesis Reactions Jennifer E. Farrugia October 29, 2003 Steric and Electronic Controllers How do substrate sterics affect the reactivity/ selectivity
I. Introduction. Peng Zhao. Liu lab
Asymmetric Total Synthesis of Mycoleptodiscin A Shupeng Zhou, Hao Chen, Yijie Luo, Wenhao Zhang and Ang Li Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai
Total Syntheses of Nominine
Total Syntheses of ominine i Literature t Group eting Lizzie Bryan ctober 17, 2007 Aconite Alkaloids Atidane V eatchane Cycloveatchane Aconitane etisan Muratake,. M.; atsume, M.; akai,. Tetrahedron, 2006,
Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-
Literature Report Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)- aseseazines A and B Reporter: Mu-Wang Chen Checker: Zhang-Pei Chen Date: 2013-05-28 Reisman,
Total Synthesis of Oxazolomycin A
Total Synthesis of xazolomycin A Me xazolomycin A Me Eto, K.; Yoshino, M.; Takahashi K.; Ishihara, J.; atakeyama S. rg. Lett. 2011, 13, 5398 Dimas Paz Wipf group- Current Literature ctober 8, 2011 Dimas
(+)-Saxitoxin : A First and Second Generation Stereoselective Synthesis
(+)-Saxitoxin : A First and Second Generation Stereoselective Synthesis Fleming, J. J.; McReynolds, M. D.; Du Bois, J. J. Am. Chem. Soc. 2007, 129, 9964. Literature Presentation Zhenjie Lu Sep 28, 2007
Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles
Supporting Information for Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Xiao-Li Lian, Zhi-Hui Ren, Yao-Yu
Palladium-Catalyzed Alkylarylation of Acrylamides with
Supporting Information Palladium-Catalyzed Alkylarylation of Acrylamides with Unactivated Alkyl Halides Hua Wang, Li-a Guo, and Xin-Hua Duan* Department of Chemistry, School of Science and ME Key Laboratory
10.5 Catalytic reactions Catalyzed reactions. Out-class extensive reading: Levine, p Catalysis Enzyme catalysis
10.5 Catalytic reactions Catalyzed reactions Out-class extensive reading: Levine, p.577 17.16 Catalysis 17.17 Enzyme catalysis 5.1 Catalysts and catalysis Catalyst A substance of small amount that can
Total Syntheses of Minfiensine
Total Syntheses of Minfiensine Douany, A. B.; umphreys, P. G.; verman, L. E.*; Wrobelski, A. D., J. Am. Chem. Soc. 2008, ASAP. D: 10.1021/ja800163v Shen, L.; Zhang, M.; Wu, Y.; Qin, Y.*, Angew. Chem. nt.
Chem ORGANIC CHEMISTRY I
ORGANIC CHEMISTRY I CHEM 221 /4 02 Final Examination April 20, 2005 0900-1200 Dr. Cerrie ROGERS x x periodic table & pk a data table provided non-programmable calculators allowed molecular model kits allowed
C H activation of aliphatic amines without unnecessary mask M2 Takaya Togo
C H activation of aliphatic amines without unnecessary mask 2017.11.25 M2 Takaya Togo 1 Outline 1.Introduction 2.Free amines as DG Discovery of new activation mode Mechanistic studies Application of the
ALDEHYDES AND KETONES
ALDEHYDES AND KETONES IN WEEK 1, A STUDENT SHOULD BE ABLE TO: 1. Give the IUPAC name given the structure, and draw the structure given the name, of aldehydes and ketones. Also, draw the structure given
Transition Metal-Catalyzed 1,2-Diamination of Alkenes. Group Meeting Timothy Chang
Transition Metal-Catalyzed 1,2-Diamination of Alkenes Group Meeting Timothy Chang 04-27-10 Valuable 1,2-Diamine Motif H H S Biotin CH H H Pt Eloxatin (Anticaner) H 2 AcH CHEt 2 Tamiflu (Antiviral) Et Ph
Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides
Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides The MIT Faculty has made this article openly available. Please share how this access benefits you. Your story matters. Citation
Total Synthesis of (-)-Mersicarpine
Total Synthesis of (-)-Mersicarpine Rie akajima, Tsuyoshi gino, Satoshi Yokoshima, and Tohru Fukuyama. J. Am. Chem. Soc. ASAP Published online 1-7-2010 Eric E. Buck Current Literature January 23, 2010
Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data
Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2012 Supplementary data Cu-catalyzed in situ generation of thiol using xanthate as thiol
Self-stable Electrophilic Reagents for Trifluoromethylthiolation. Reporter: Linrui Zhang Supervisor: Prof. Yong Huang Date:
Self-stable Electrophilic Reagents for Trifluoromethylthiolation Reporter: Linrui Zhang Supervisor: Prof. Yong Huang Date: 2017-12-25 Content Introduction Trifluoromethanesulfenates: Preparation and reactivity
Anti-Markovnikov Olefin Functionalization
Anti-Markovnikov Olefin Functionalization ~Prof. Robert H. Grubbs Work~ 4 th Literature Seminar July 5, 2014 Soichi Ito (D1) Contents 1. Introduction Flow of Prof. Grubbs Research Markovnikov s Rule Wacker
C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals. Phil Knutson Ferreira Group 12/3/2015
C H Bond Functionalization: New Strategies for the Synthesis of Complex Natural Products and Pharmaceuticals Phil Knutson Ferreira Group 12/3/2015 New strategies in organic synthesis nsf-cchf.com What
Palladium-Catalyzed Oxygenation of Unactivated sp 3 C-H Bonds
Palladium-Catalyzed xygenation of Unactivated sp 3 C- Bonds Pd(Ac) 2 5 mol% PhI(Ac) 2 1.1 eq. Pd 2 Ac Desai, L. P.; ull, K. L.; Sanford *, M. S. University of Michigan J. Am. Chem. Soc. 2004, 126, ASAP
Accessory Information
Accessory Information Synthesis of 5-phenyl 2-Functionalized Pyrroles by amino Heck and tandem amino Heck Carbonylation reactions Shazia Zaman, *A,B Mitsuru Kitamura B, C and Andrew D. Abell A *A Department
Rh(III)-catalyzed C-H Activation and Annulation via Oxidizing Directing Group. Lei Zhang 03/23/2016 Dong Group
Rh(III)-catalyzed C-H Activation and Annulation via Oxidizing Directing Group Lei Zhang 03/23/2016 Dong Group Content 1 Alkyne involved Annulation in Hua group 2 3 4 Brief Introduction of Internal Oxidants
A Modular Approach to Polyketide Building Blocks: Cycloadditions of Nitrile Oxides and Homoallylic Alcohols
A Modular Approach to Polyketide Building Blocks: Cycloadditions of itrile xides and Homoallylic Alcohols rganic Letters, 2005, ASAP ina Lohse-Fraefel and Erick M. Carreira * H H H + ' 1. t-bucl, -78 C
Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization
![Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization](/thumbs/82/85235286.jpg "Total Synthesis of (+/-)-Goniomitine via a Formal Nitrile/Donor-Acceptor Cyclopropane [3 + 2] Cyclization")
Total Synthesis of (+/-)-Goniomitine via a Formal itrile/donor-acceptor Cyclopropane [3 + 2] Cyclization (-)-Goniomitine Christian L. Morales and Brian Pagenkopf* rganic Letters, ASAP Current Literature
Nucleophilic Fluorination. Souvik Rakshit Burke group Literature Seminar July 13, 2013
Nucleophilic Fluorination Souvik Rakshit Burke group Literature Seminar July 13, 2013 Relevance 20% of pharmaceuticals contain fluorine 5-fluorouracil Antineoplastic agent, 1957 Lipitor (Atorvastatin)
Organic Chemistry Laboratory Summer Lecture 6 Transition metal organometallic chemistry and catalysis July
344 Organic Chemistry Laboratory Summer 2013 Lecture 6 Transition metal organometallic chemistry and catalysis July 30 2013 Summary of Grignard lecture Organometallic chemistry - the chemistry of compounds
Total Synthesis of the Caged Indole Alkaloid Arboridinine Enabled by aza-prins and Metal-Mediated Cyclizations
Total Synthesis of the Caged Indole Alkaloid Arboridinine Enabled by aza-prins and Metal-Mediated Cyclizations Bart Herleì, Martin J. Wanner, Jan H. van Maarseveen, and Henk Hiemstra DOI: 10.102 jacs.7b07724
Manganese-Catalyzed Late- Stage Aliphatic C H Azidation
Wipf group current literature Manganese-Catalyzed Late- Stage Aliphatic C H Azidation J. Am. Chem. Soc. 2015, 137, 5300 5303 Xiongyi Huang, Tova M. Bergsten, and John T. Groves Department of Chemistry,
Copper-Catalyzed Reaction of Alkyl Halides with Cyclopentadienylmagnesium Reagent
Copper-Catalyzed eaction of Alkyl Halides with Cyclopentadienylmagnesium eagent Mg 1) cat. Cu(Tf) 2 i Pr 2, 25 o C, 3 h 2) H 2, Pt 2 Masahiro Sai, Hidenori Someya, Hideki Yorimitsu, and Koichiro shima
Supporting Information
1 Supporting Information Gold-catalyzed Synthesis of 3-arylindoles via Annulation of Nitrosoarenes and Alkynes Siva Murru, August A. Gallo and Radhey S. Srivastava* Department of Chemistry, University
Lewis Base Activation of Lewis Acids: Development of a Lewis Base Catalyzed Selenolactonization
Lewis Base Activation of Lewis Acids: Development of a Lewis Base Catalyzed Selenolactonization Denmark, S.E. and Collins, W.R. rg. Lett. 2007, 9, 3801-3804. C 2 H + Se Lewis Base CH 2 Cl 2 Se Presented
Alcohols, Ethers and Epoxides. Chapter Organic Chemistry, 8th Edition John McMurry
Alcohols, Ethers and Epoxides Chapter 17-18 Organic Chemistry, 8th Edition John McMurry 1 Introduction Structure and Bonding Alcohols contain a hydroxy group (OH) bonded to an sp 3 hybridized carbon. 2
Design and Synthesis of Novel Benzimidazoles and Analogues of Potential Anthelmintic Activity
Mansoura University Pharm. Organic. Chem. Dept. Design and Synthesis of ovel Benzimidazoles and Analogues of Potential Anthelmintic Activity Thesis Presented By Basem Awad Mansour Mohamed B. Pharm. Sci.,
Recent Developments in Alkynylation
--New approaches to introduce an alkynyl group Reporter: Zhao-feng Wang Supervisor: Yong Huang 2013-03-27 Contents 1. Introduction of Acetylene Chemistry 2. Nucleophilic alkynylation : Classic text book
Galbulimima Alkaloids (-)-GB 13 and (+)-GB 16
Galbulimima Alkaloids (-)-GB 13 and (+)-GB 16 Zi, W.; Yu, S.; Ma, D. Angew. Chem. Int. Ed. 2010, 49, 5887 5890 Current Literature Jie Xu 08.28.10 Jie Xu @ Wipf Group Page 1 of 18 12/5/2010 Isolation Galbulimima
SUPPORTING INFORMATION
SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry
Heterocyclic Chemistry Midterm Examination. 3 May Professor Baran Department of Chemistry The Scripps Research Institute
eterocyclic Chemistry Midterm Examination 3 May 2013 Professor Baran Department of Chemistry The cripps Research Institute ame: Last 4 digits of your ocial ecurity #: This is a 2-hour test that you have
Synthesis of Amphidinolide X and an Exploration of Key Reactions
PJM 1/12/05 Synthesis of Amphidinolide X and an Exploration of Key eactions Lepage,.; Kattnig, E.; Furstner, A. JACS, 2004, 126, 15970-15971. 7 13 1 6 19 - Produced by marine dinoflagellates, Amphidinium
Palladium-Catalyzed Electrophilic Aromatic C H Fluorination
Palladium-Catalyzed Electrophilic Aromatic C luorination +2 Pd II 2 B 4 C (5 mol %) SI (2 eq) MeC, rt 61%, 69:31 o:p C Yamamoto, K; Li, J.; Garber, J. A..; Rolfes, J. D.; Boursalian, G. B.; Borghs, J.
Asymmetric Synthesis of Medium-Sized Rings by Intramolecular Au(I)-Catalyzed Cyclopropanation
Asymmetric Synthesis of Medium-Sized ings by Intramolecular Au(I)-Catalyzed Cyclopropanation 1 2 Iain D. G. Watson, Stefanie itter, and F. Dean Toste JACS, ASAP, 1/22/2009 DI: 10.1021/ja8085005 2.5 mol%
1. Determine the oxidation state of the metal centre and count the number of electrons.
Exercise sheet : Organometallic chemistry Gunnar Bachem 1. Determine the oxidation state of the metal centre and count the number of electrons. 2. The metal fragment 1 reacts with the amine to give a carbene
Converting Cycloalkanones into N- Heterocycles: Formal Synthesis of ( )-Gephyrotoxin 287C. Claude Spino et al., J. Org. Chem. 2013, 78,
Converting Cycloalkanones into N- Heterocycles: Formal Synthesis of ( )-Gephyrotoxin 287C Claude Spino et al., J. Org. Chem. 2013, 78, 12532 12544. Poison frog alkaloids Isolated from poison frog skin.
SYNTHESIS AND CHARACTERIZATION OF SOME NICKEL (II) COMPLEXES VIA BIOACTIVE SCHIFF BASES
SYTHESIS AD CHAACTEIZATIO OF SOME ICKEL (II) COMPLEXES VIA BIOACTIVE SCHIFF BASES Prof. Mehreen Dawre Assi. Prof. D. G. Tatkare Mahavidyalay, Mangaon-aigad Abstract A large number of Schiff bases and their
Standardized Representations of ELN Reactions for Categorization and Duplicate/Variation Identification
Standardized Representations of ELN Reactions for Categorization and Duplicate/Variation Identification Roger Sayle and daniel lowe NextMove Software, Cambridge, UK Overview Electronic Lab Notebooks (ELNs)
Homogeneous Catalysis - B. List
omogeneous Catalysis - B. List 2.2.2 Research Area "rganocatalytic Asymmetric α-alkylation of Aldehydes" (B. List) Involved:. Vignola, A. Majeed Seayad bjective: α-alkylations of carbonyl compounds are
Iridium-Catalyzed Hydrogenation with Chiral P,N Ligands
Iridium-Catalyzed Hydrogenation with Chiral P, Ligands 贾佳 utline Brief Introduction Hydrogenation of C=C Bonds Hydrogenation of C= Bonds Hydrogenation of C= Bonds Conclusion Brief Introduction First example
Chem 1075 Chapter 19 Organic Chemistry Lecture Outline
Chem 1075 Chapter 19 Organic Chemistry Lecture Outline Slide 2 Introduction Organic chemistry is the study of and its compounds. The major sources of carbon are the fossil fuels: petroleum, natural gas,
Amines. Amines are organic compounds containing a nitrogen functionality. primary secondary tertiary quaternary
Amines Amines are organic compounds containing a nitrogen functionality Depending upon the number of alkyl, or aryl, groups attached to nitrogen determines its classification, or order 2 primary secondary
An Eco-friendly Route to Synthesis of Quinolines
An Eco-friendly Route to Synthesis of Quinolines A.D. Mishra Department of Chemistry, Tribhuvan University, P.N. Campus, Pokhara, Nepal E-mail: mishraad05@hotmail.com Abstract Some 2-hydroxy-4-methyl-6-
Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid
Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid Shiqing Xu, Akimichi Oda, Thomas Bobinski, Haijun Li, Yohei Matsueda, and Ei-ichi Negishi Angew. Chem. Int. Ed. 2015,
Available chemicals from the catalog (the starting sources of carbon compounds will continually decrease as we learn new reactions.
ucleophilic ubstitution & Elimination Chemistry Beauchamp 1 Available chemicals from the catalog (the starting sources of carbon compounds will continually decrease as we learn new reactions. ources of
The version of SI posted May 6, 2004 contained errors. The correct version was posted October 21, 2004.
The version of SI posted May 6, 2004 contained errors. The correct version was posted October 21, 2004. Sterically Bulky Thioureas as Air and Moisture Stable Ligands for Pd-Catalyzed Heck Reactions of
Journal of Chemical and Pharmaceutical Research
Available online www.jocpr.com Journal of Chemical and Pharmaceutical Research ISSN No: 0975-7384 CODEN(USA): JCPRC5 J. Chem. Pharm. Res., 2011, 3(5):519-523 Indole: The molecule of diverse pharmacological
Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo
Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo 2014.1.6 1 Content Introduction Progress of Catellani Reaction o-alkylation and Applications o-arylation and Applications Conclusion and Outlook
Aza-Wacker-Type Cyclization. Group Meeting Tuesday, April 19, 2011 William Kuester
Aza-Wacker-Type Cyclization Group Meeting Tuesday, April 19, 2011 William Kuester N-heterocylization Reductive Amination Hydroamination Oxidative Cyclization Chemler, S.R. Org. Biomol. Chem. 2009, 7, 3009-3019.
Metalloporphyrin. ~as efficient Lewis acid catalysts with a unique reaction-field~ and. ~Synthetic study toward complex metalloporphyrins~
Metalloporphyrin ~as efficient Lewis acid catalysts with a unique reaction-field~ and ~Synthetic study toward complex metalloporphyrins~ Literature Seminar Kenta Saito (D1) 1 Topics Chapter 1 ~as efficient
CHEM 203. Final Exam December 15, 2010 ANSWERS. This a closed-notes, closed-book exam. You may use your set of molecular models
CEM 203 Final Exam December 15, 2010 Your name: ANSWERS This a closed-notes, closed-book exam You may use your set of molecular models This test contains 15 pages Time: 2h 30 min 1. / 16 2. / 15 3. / 24
Stereoselective Allylation of Imines. Joshua Pierce Research Topic Seminar
Stereoselective Allylation of Imines Joshua Pierce esearch Topic Seminar 10-30-04 Josh Pierce @ Wipf Group 1 11/3/2004 Topic Overview: Introduction Imines: Why is C=N different? Synthesis of Allylating
R 2 R 4 Ln catalyst. This manuscript describes the methods for the synthesis and application of group 4 metallocene bis(trimethylsilyl)acetylene
VII Abstracts 2011 p1 2.12.15 rganometallic Complexes of Scandium, Yttrium, and the Lanthanides P. Dissanayake, D. J. Averill, and M. J. Allen This manuscript is an update to the existing Science of Synthesis
Aziridine Carboxylates, Carboxamides and Lactones: New Methods for Their Preparation and Their Transformation into α- and β-amino Acid Derivatives
Molecules 2000, 5 293 Aziridine Carboxylates, Carboxamides and Lactones: ew Methods for Their Preparation and Their Transformation into α- and β-amino Acid Derivatives obert H. Dodd Institut de Chimie
Heterocyclic Chemistry
Dr. P. Wipf Page 1 of 8 10/24/2009 eterocyclic Chemistry Most Common Aromatic Scaffolds Present in Bioactive Molecules S S S S rtl, P.; Jelfs, S.; Muehlbacher, J.; Schuffenhauer, A.; Selzer, P., "Quest
Cobalt Catalysed Organic Reactions
Department of Chemistry and Biochemistry, University of Bern Topic review Cobalt Catalysed Organic Reactions Group of Prof. Philippe Renaud Andrey S. Kuzovlev 29.01.2015 ... we invite the attention of
Enantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition
Chapter 9 Alkynes. Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Chapter 9 Alkynes Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display. 9.1 Sources of Alkynes Acetylene Industrial preparation of acetylene is by dehydrogenation of
Heterocyclic Chemistry - Midterm. May 6 th, Professor Baran Department of Chemistry The Scripps Research Institute
eterocyclic Chemistry - Midterm May 6 th, 2008 Professor Baran Department of Chemistry The cripps Research Institute ame: Last 4 digits of your ocial ecurity #: This is an open-notes exam designed to last
Total Synthesis of ( )-Nakadomarin A
Total Synthesis of ( )-Nakadomarin A Pavol Jakubec, Dane M. Cockfield, and Darren J. Dixon University of Oxford and University of Manchester, UK J. Am. Chem. Soc. 2009, ASAP DOI: 10.1021/ja908399s Marie-Céline
Physical Properties. Alcohols can be: CH CH 2 OH CH 2 CH 3 C OH CH 3. Secondary alcohol. Primary alcohol. Tertiary alcohol
Chapter 10: Structure and Synthesis of Alcohols 100 Physical Properties Alcohols can be: CH 3 CH 3 CH CH 2 OH * Primary alcohol CH 3 OH CH * CH 2 CH 3 Secondary alcohol CH 3 CH 3 * C OH CH 3 Tertiary alcohol
Intramolecular Ene Reactions Utilizing Oxazolones and Enol Ethers Fisk, J.S. and Tepe, J..J J. Am. Chem. Soc., 2007, 129,
Intramolecular Ene Reactions Utilizing xazolones and Enol Ethers Fisk, J.S. and Tepe, J..J J. Am. Chem. Soc., 2007, 129, 3058-3059 - versus -Arylation of Aminoalcohols: rthogonal Selectivity in Copper-Based
SUPPORTING INFORMATION
Eur. J. Org. Chem. 2004 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2004 ISSN 1434 193X SUPPORTING INFORMATION Title: The (Schiff base)vanadium(v) Complex Catalyzed Oxidation of Bromide A New Method
Incontro per l orientamento alla tesi sperimentale
Corso di Laurea Magistrale in Chimica e Tecnologia del armaco Corso di Laurea Magistrale in armacia Incontro per l orientamento alla tesi sperimentale Prof.ssa Daniela Lanari 22 ovembre 2017, Aula A via
Total Synthesis of ( )-Virginiamycin M2
Total Synthesis of ( )-Virginiamycin M2 Jie Wu and James S. Panek, Angewandte Chemie International Edition, 2010, 49, 6165-6168 btained from the CDC Public ealth Image Library. Image credit: CDC/Dr. David