Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S
|
|
- Morris Horn
- 5 years ago
- Views:
Transcription
1 Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS (5 ml) was stirred for 1 h, then a solution of (2R,3R)-butanediol dimesylate (0.531 g, 2.2 mmol) in DMS (10 ml) was added dropwise into this mixture over a period of 4 h. The mixture was continuously stirred at 55 C for 8 h before pouring into water (100 ml). The organic phase was extracted with CH 2 Cl 2. The extract was treated with 2 N HCl solution (10 ml) and washed with water and brine again. The organic layer was separated, dried over Na 2 S 4, and concentrated in vacuo. The residue was purified through a silica gel column to give a colorless oil 3 (0.461 g, 1.15 mmol, 53% yield). 1 H NMR (500 MHz, CDCl 3 ): δ = 1.36 (d, J = 6.0 Hz, 6H), (m, 2H), (m, 2H) and (m, 6H). 13 C NMR (125 MHz, CDCl 3 ): δ = 15.27, 76.34, , , , , and HRMS (EI + VE + LMR): calcd for C 16 H 16 Br 2 2 [M] , found [α] 20 D = 22.6 (c = 1, CHCl 3 ). Synthesis of (2S,3S)-2,3-bis[3-(diphenylphosphoryl)phenoxy]butane (5). Compound 3 (1.80 g, 4.50 mmol) was azeotropically dried with dry toluene (15 ml 2) and dissolved in dry tetrahydrofuran (THF) (100 ml). n-buli (9.45 mmol, 1.6 M solution in hexane) was added dropwise into the solution at 78 C within 30 min under N 2. After stirring for an additional 1 h at this temperature, chlorodiphenyl phosphine (1.8 ml, 9.45 mmol) in THF (5 ml) was added dropwise to the resulting mixture. The reaction was continued at 78 C for 1 h and then at room temperature overnight. The resulting light-yellow solution was extracted with CH 2 Cl 2 /water. The organic phase was separated, washed with water and brine, and dried over Na 2 S 4. After evaporation of the solvent, a light-yellow solid was obtained. The residue was purified by silica gel column chromatography to give a colorless oily solid 4. An aqueous H 2 2 solution (30%, 6.0 ml) was added to a solution of compound 4 in acetone (20 ml) at 0 C. The reaction was monitored by thin-layer chromatography. The product was extracted with dichloromethane twice. The combined extract was washed successively with Na 2 S 2 3 solution, water, and brine, dried over anhydrous Na 2 S 4, and was concentrated in vacuo to give a crude product. Purification by silica gel column chromatography afforded a pure colorless solid 5 (2.46 g, 3.83 mmol, 85% yield based on 3). 1 H NMR (500 MHz, CDCl 3 ): δ = 1.26 (d, J = 5.5 Hz, 6H), (m, 2H), (m, 2H), (dd, J = 11.8 Hz, 7.8 Hz, 2H), (m, 4H), (m, 8H), (m, 4H) and (m, 8H). 31 P NMR (202 MHz, CDCl 3 ): δ = C NMR (125 MHz, CDCl 3 ): δ = 15.06, 76.03, , , , , , , , , , , , , , , , , , and HRMS (ESI): calcd for C 40 H 37 P 2 4 [M + H] , found ; [α] 20 D = 19.6 (c = 1, CHCl 3 ). Preparation of RuLCl 2 (DMF) n. To a Schlenk tube with a magnetic stirring bar was charged with [RuCl 2 (benzene)] 2 (2.0 mg, mmol), ligand 8 (5.4 mg, mmol), 2,2 -bis(diphenylphosphino)-6,6 -dimethoxy-1,1 -biphenyl (Me-BIPHEP) (4.9 mg, mmol) or (S)-2,2 -bis(diphenylphosphino)-1,1 -binaphthyl (S-BINAP) (5.3
2 mg, mmol), and degassed dry dimethylformamide (DMF) (2.0 ml). The resulting solution was heated at 100 C for 30 min and then was concentrated in vacuo to give the catalyst as a reddish-brown solid. Preparation of [RuL(p-cymene)Cl]Cl. To a mixture of the ligand (8 8.4 mg, S-BINAP 8.6 mg, or Me-BIPHEP 8.1 mg, mmol) and [Ru(p-cymene)Cl 2 ] 2 (3.7 mg, mmol) in a Schlenk tube was added ethanol (3.0 ml) and CH 2 Cl 2 (1.0 ml). The resulting mixture was stirred at 50 C for 1 h and was filtered. The orange-yellow filtrate was concentrated in vacuo to give the catalyst as an orange solid. [Ru(R)-8(p-cymene)Cl]Cl: 1 H NMR (500 MHz, CD 2 Cl 2 ): δ = 0.90 (d, J = 6.5 Hz, 3H), 1.12 (d, J = 6.5 Hz, 3H), 1.16 (d, J = 6.0 Hz, 3H), 1.29 (d, J = 7.0 Hz, 3H), 1.87 (s, 3H), (m, 1H), (m, 1H), (m, 1H), 6.02 (d, J = 7 Hz, 1H), 6.58 (d, J = 8 Hz, 1H) and (m, 28 H). 31 P NMR (202 MHz, CDCl 3 ): δ = (d, J = 65.8 Hz), (d, J = 65.8 Hz). Preparation of [Ru8(η 6 -C 6 H 6 )Cl]Cl. Preparation method of catalyst [Ru8(η 6 - C 6 H 6 )Cl]Cl was similar to that for [RuL(p-cymene)Cl]Cl using [Ru(benzene)Cl 2 ] 2 and ligand 8 as starting materials. [Ru8(η 6 -C 6 H 6 )Cl]Cl: 1 H NMR (500 MHz, CD 2 Cl 2 ): δ = 1.17 (d, J = 6.5 Hz, 3H), 1.18 (d, J = 6.5 Hz, 3H), (m, 1H), (m, 1H), 5.80 (s, 6H) and (m, 26H). 31 P NMR (202 MHz, CD 2 Cl 2 ): δ = (d, J = 68.4 Hz), (d, J = 68.4 Hz). Preparation of (NMe 2 H 2 )[(Ru8Cl) 2 (µ-cl) 3 ]. To a mixture of the ligand 8 (10 mg, mmol) and [Ru(benzene)Cl 2 ] 2 (4.1 mg, mmol) in a Schlenk tube was added ethanol (3.0 ml) and CH 2 Cl 2 (1.0 ml). The resulting mixture was stirred at 50 C for 1 h. The solvent was removed in vacuo, then dimethylamine hydrochloride (1.4 mg, mmol) and dioxane (5 ml) were added. The mixture was stirred under reflux for 15 h. The reaction solution was concentrated in vacuo to dryness to afford the catalyst as a brown solid. (NMe 2 H 2 )[(Ru8Cl) 2 (µ-cl) 3 ]: 1 H NMR (500 MHz, CD 2 Cl 2 ): δ = 1.20 (d, J = 6 Hz, 6 H), 1.29 (d, J = 6.5 Hz, 6H), 3.56 (s, 6H), (m, 2H), (m. 2H), (m, 2H), (d, 8 Hz, 2H), (m, 4H), (m, 2H), (m, 6H), 6.89 (t, J = 8 Hz, 2 H), (m, 6 H), (m, 12 H), (m, 8H), 7.86 (t, J = 8.3 Hz, 4H) and (broad s, 6 H). 31 P NMR (202 MHz, CD 2 Cl 2 ): δ = (d, J = 38.8 Hz), (d, J = 38.8 Hz). General Procedure for the Asymmetric Hydrogenation of β-ketoesters. A glass-lined stainless steel autoclave was charged with β-ketoester (0.5 mmol), RuLCl 2 (DMF) n ( mmol), CH 2 Cl 2 (12.5 µl) and methanol or ethanol (987.5 µl) under nitrogen atmosphere. The mixture was stirred well with a magnetic stirrer at a certain temperature under 50 psi H 2. Conversions of the substrates and enantiomeric excesses of the products
3 were determined by GC after converting the products to the corresponding acetyl derivatives or by HPLC. General Procedure for the Asymmetric Hydrogenation of α-ketoester. A glass-lined stainless steel autoclave was charged with α-ketoester (0.5 mmol), [Ru8(η 6 -C 6 H 6 )Cl]Cl ( mmol), and methanol (1 ml) under nitrogen atmosphere. The mixture was stirred well with a magnetic stirrer at a certain temperature under a certain hydrogenation pressure. Conversions of the substrates and enantiomeric excesses of the products were determined by GC. General Procedure for the Asymmetric Hydrogenation of 2-(6 -Methoxy-2 - naphthyl)propenoic Acid. A glass-lined stainless steel reactor was charged with 5.0 mg of 2-(6 -methoxy-2 -naphthyl)propenoic acid, mmol [RuL(p-cymene)Cl]Cl catalyst and 2.5 ml of methanol. The solution was stirred well with a magnetic stirrer at a certain temperature under a chosen hydrogen pressure. Conversion of the substrate and enantiomeric excess of the product were determined by HPLC with a Sumichiral A column. General Procedure for the Asymmetric Hydrogenation of β-(acylamino)acrylates. A glass-lined stainless steel autoclave was charged with β-(acylamino)acrylates (1.7 mg), [Ru8(η 6 -C 6 H 6 )Cl]Cl (S/C = 100:1) and methanol under nitrogen atmosphere. The mixture was stirred well with a magnetic stirrer at a certain temperature under 250 psi H 2. Conversions of the substrates and enantiomeric excesses of the products were determined by GC. General Procedure for the Asymmetric Hydrogenation of Enol Acetates. A glasslined stainless steel autoclave was charged with enol acetates (0.1 mmol) in ethanol (1.0 ml) and (NMe 2 H 2 )[(Ru8Cl) 2 (µ-cl) 3 ] ( mmol) in CH 2 Cl 2 (0.25 ml) under nitrogen atmosphere. The mixture was stirred well with a magnetic stirrer at a room temperature (rt) to 50 C under 50 psi H 2. Conversions of the substrates and enantiomeric excesses of the products were determined by chiral GC with a Varian 25 m 0.25 mm CP- CYCLDEX B 236M column.
4 1 H NMR (500 MHz, CDCl 3 ) of 3 Br Br
5 13 C NMR (125 MHz, CDCl 3 ) of 3 Br Br
6 1 H NMR (500 MHz, CDCl 3 ) of 5 Ph 2 ()P Ph 2 ()P
7 31 P NMR (202 MHz, CDCl 3 ) of 5 Ph 2 ()P Ph 2 ()P
8 13 C NMR (125 MHz, CDCl 3 ) of 5 Ph 2 ()P Ph 2 ()P
9 1 H NMR (500 MHz, CDCl 3 ) of 6 Ph 2 P() Ph 2 P() I I
10 31 P NMR (202 MHz, CDCl 3 ) of 6 Ph 2 P() Ph 2 P() I I
Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12
Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents
More informationThe First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C
Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,
More informationAn Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL
More informationSupporting Information
Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,
More informationSupporting Information
Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and
More informationFormal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis
Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,
More informationOpioid ligands with mixed properties from substituted enantiomeric N-phenethyl-5-
Supplementary Information for: Opioid ligands with mixed properties from substituted enantiomeric N-phenethyl-5- phenylmorphans. Synthesis of a μ-agonist δ antagonist and δ-inverse agonists Kejun Cheng,
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic
More informationSupporting Information:
Enantioselective Synthesis of (-)-Codeine and (-)-Morphine Barry M. Trost* and Weiping Tang Department of Chemistry, Stanford University, Stanford, CA 94305-5080 1. Aldehyde 7. Supporting Information:
More information1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in
Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow
More informationSupporting Information. (1S,8aS)-octahydroindolizidin-1-ol.
SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.
More informationCompound Number. Synthetic Procedure
Compound Number 1 2 3 4 5 Synthetic Procedure Compound 1, KY1220, (Z)-5-((1-(4-nitrophenyl)-1H-pyrrol-2-yl)methylene)-2-thioxoimidazolidin-4-one was purchased from Chemdiv, Catalog #3229-2677, 97% HPLC
More informationSupporting 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
More informationPhotooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins
S1 Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins Antonia Kouridaki, Tamsyn Montagnon, Maria Tofi and Georgios Vassilikogiannakis* Department of
More informationSupporting Information For:
Supporting Information For: Peptidic α-ketocarboxylic Acids and Sulfonamides as Inhibitors of Protein Tyrosine Phosphatases Yen Ting Chen, Jian Xie, and Christopher T. Seto* Department of Chemistry, Brown
More informationChia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo and Yun Chen*
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Supporting Information Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization
More informationSupplementary Information. Table of Contents
Supplementary Information Modular Chiral Dendritic monodentate phosphoramidite ligands for Rh(I)-Catalyzed Asymmetric Hydrogenation: Unprecedented Enhancement of Enantioselectivity Feng Zhang, a, b Yong
More informationSupporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials
Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde
More informationSupporting Information
Supporting Information Precision Synthesis of Poly(-hexylpyrrole) and its Diblock Copolymer with Poly(p-phenylene) via Catalyst-Transfer Polycondensation Akihiro Yokoyama, Akira Kato, Ryo Miyakoshi, and
More informationhydroxyanthraquinones related to proisocrinins
Supporting Information for Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins Joyeeta Roy, Tanushree Mal, Supriti Jana and Dipakranjan Mal* Address: Department of Chemistry,
More informationBlock: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection
Electronic Supplementary Information (ESI) Luminogenic Materials Constructed from Tetraphenylethene Building Block: Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and
More informationTetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon
SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone
More informationSupporting Information
Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,
More informationSupplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)
Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and
More informationSynthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity
Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic
More informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany rganocatalytic Conjugate Addition of Malonates to a,ß-unsaturated Aldehydes: Asymmetric Formal Synthesis of (-)-Paroxetine, Chiral Lactams
More informationSynthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes
Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi
More informationHow to build and race a fast nanocar Synthesis Information
How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,
More informationSupporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A
Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:
More informationOrganocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine
Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine Ying Xie, a Hongjie Pan, a Xiao Xiao, a Songlei Li a and Yian Shi* a,b a Beijing National Laboratory for
More informationSupporting Information. Rhodium, iridium and nickel complexes with a. 1,3,5-triphenylbenzene tris-mic ligand. Study of
Supporting Information for Rhodium, iridium and nickel complexes with a 1,3,5-triphenylbenzene tris-mic ligand. Study of the electronic properties and catalytic activities Carmen Mejuto 1, Beatriz Royo
More informationSUPPORTING 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
More informationA fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media
Supplementary Information A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media Weiwei Wang and Quanrui Wang* Department of Chemistry,
More informationSupporting Information
Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook
More informationEffect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted
More informationSUPPLEMENTARY INFORMATION
Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using
More informationSupporting Information
Supporting Information Control the Structure of Zr-Tetracarboxylate Frameworks through Steric Tuning Jiandong Pang,,,,# Shuai Yuan,,# Junsheng Qin, Caiping Liu, Christina Lollar, Mingyan Wu,*, Daqiang
More informationTriazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3
Triazabicyclodecene: an Effective Isotope Exchange Catalyst in CDCl 3 Supporting Information Cyrille Sabot, Kanduluru Ananda Kumar, Cyril Antheaume, Charles Mioskowski*, Laboratoire de Synthèse Bio-rganique,
More informationSupporting information. Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation.
Supporting information Enantioselective synthesis of 2-methyl indoline by palladium catalysed asymmetric C(sp 3 )-H activation/cyclisation Saithalavi Anas, Alex Cordi and Henri B. Kagan * Institut de Chimie
More informationSupplementary Note 2. Synthesis of compounds. Synthesis of compound BI Supplementary Scheme 1: Synthesis of compound BI-7273
Supplementary ote 2 Synthesis of compounds Synthesis of compound I-7273 H HMe 2 *HCl aac, AcH 4 7 ah(ac) 3 ah, MeI CH 2 Pd 2 (dba) 3, KAc, X-Phos 1,4-dioxane 5 6 8 + Pd(dppf) *CH 2 a 2 C 3 DMF I-7273 (2)
More informationEnantioselective Organocatalytic Michael Addition of Malonate Esters to Nitro Olefins Using Bifunctional Cinchonine Derivatives
Enantioselective rganocatalytic Michael Addition of Malonate Esters to itro lefins Using Bifunctional Cinchonine Derivatives Jinxing Ye, Darren J. Dixon * and Peter S. Hynes School of Chemistry, University
More informationSupporting Information for
Electronic Supplementary Material (ES) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Supporting nformation for BODPY-Containing
More informationSensitive and reliable detection of glass transition of polymers. by fluorescent probes based on AIE luminogens
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting information Sensitive and reliable detection of glass transition of polymers
More informationSUPPLEMENTARY INFORMATION
Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Diphenylprolinol Silyl Ether in Enantioselective, Catalytic Tandem Michael-Henry Reaction for the Control of Four Stereocenters Yujiro Hayashi*,
More informationSupplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol.
Tetrahedron Letters 1 Pergamon TETRAHEDRN LETTERS Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Jennifer L. Stockdill,
More informationSupporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003
Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Enantioselective Synthesis of Axially Chiral Vinyl arenes through Palladium-catalyzed
More informationSupporting Information
Supporting Information Total Synthesis and Structural Reassignment of (±)-Cereoanhydride Zhiqiang Ren, Yu Hao, Xiangdong Hu* Department of Chemistry & Material Science, Key Laboratory of Synthetic and
More informationDivergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site
More informationSupporting Information
Supporting Information ACA: A Family of Fluorescent Probes that Bind and Stain Amyloid Plaques in Human Tissue Willy M. Chang, a Marianna Dakanali, a Christina C. Capule, a Christina J. Sigurdson, b Jerry
More informationStoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes to Borinic Esters Lauren E. Longobardi, Connie Tang, and Douglas W.
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Supplementary Data for: Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes
More informationMolecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe
Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments
More informationTable of Contents 1. General procedure for the chiral phosphoric acid catalyzed asymmetric reductive amination using benzothiazoline
Enantioselective Organocatalytic Reductive Amination of Aliphatic Ketones by Benzothiazoline as Hydrogen Donor Kodai Saito, Takahiko Akiyama* Department of Chemistry, Faculty of Science, Gakushuin University,
More informationSupporting Information
Supporting Information Wiley-VCH 2011 69451 Weinheim, Germany Enantioselective Total Synthesis of ( )-Jiadifenolide** Jing Xu, Lynnie Trzoss, Weng K. Chang, and Emmanuel A. Theodorakis* anie_201100313_sm_miscellaneous_information.pdf
More informationwith EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15
2. A solution of Rhodamine B (14.2 g, 30.0 mmol) in CH 2 Cl 2 (40 ml) was treated with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 g, 30.0 mmol) and TEA (4.21 ml, 3.03 g, 30.0
More informationSupplementary Information (Manuscript C005066K)
Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)
More informationEnhanced Radical-Scavenging Activity of Naturally-Oriented Artepillin C Derivatives
Supporting nformation Enhanced Radical-Scavenging Activity of Naturally-Oriented Artepillin C Derivatives Sushma Manda, a kuo Nakanishi,* a,b Kei Ohkubo, b Yoshihiro Uto, c Tomonori Kawashima, b Hitoshi
More informationDistyrylbenzene-aldehydes: identification of proteins in water. Supporting Information
Electronic Supplementary Material (ESI) for Analyst. This journal is The Royal Society of Chemistry 2015 Distyrylbenzene-aldehydes: identification of proteins in water Jan Kumpf, Jan Freudenberg and Uwe
More informationSupporting Information for
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for
More informationSupporting Information for Sonogashira Hagihara reactions of halogenated glycals. Experimental procedures, analytical data and NMR spectra
Supporting Information for Sonogashira Hagihara reactions of halogenated glycals Dennis C. Koester and Daniel B. Werz* Address: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität
More informationSupporting Information
Supporting Information Selective Synthesis of [6]-, [8]-, and [10]Cycloparaphenylenes Eiichi Kayahara, 1,2 Takahiro Iwamoto, 1 Toshiyasu Suzuki, 2,3 and Shigeru Yamago* 1,2 1 Institute for Chemical Research,
More informationSynthesis and nucleophilic aromatic substitution of 3- fluoro-5-nitro-1-(pentafluorosulfanyl)benzene
Supporting Information for Synthesis and nucleophilic aromatic substitution of 3- fluoro-5-nitro-1-(pentafluorosulfanyl)benzene Javier Ajenjo 1, Martin Greenhall 2, Camillo Zarantonello 2 and Petr Beier
More informationSupporting Information
Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy
More informationAccessory 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
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Complete Switch of Migratory Aptitude in Aluminum-Catalyzed 1,2-Rearrangement of Differently α,α-disubstituted α-siloxy Aldehydes Kohsuke hmatsu,
More informationPoly(4-vinylimidazolium)s: A Highly Recyclable Organocatalyst Precursor for. Benzoin Condensation Reaction
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 24 Supporting Information Poly(4-vinylimidazolium)s: A Highly Recyclable rganocatalyst Precursor
More informationCarbonylative Coupling of Allylic Acetates with. Arylboronic Acids
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Carbonylative Coupling of Allylic Acetates with Arylboronic Acids Wei Ma, a Ting Yu, Dong Xue,*
More informationDomino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,
More informationSupporting Information for
Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,
More informationSelective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3
S1 Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 David Bézier, Sehoon Park and Maurice Brookhart* Department of Chemistry, University of North Carolina at Chapel Hill,
More informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany Engineering Polymeric Chiral Catalyst Using Hydrogen Bonding and Coordination Interactions Lei Shi, 1,2 Xingwang Wang, 1 Christian A. Sandoval,
More informationSequential dynamic structuralisation by in situ production of
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Electronic Supplementary Information Sequential dynamic structuralisation by in situ production
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Micro- and mesoporous poly(schiff-base)s
More informationSupporting Information
Supporting Information Efficient Short Step Synthesis of Corey s Tamiflu Intermediate Nsiama Tienabe Kipassa, Hiroaki kamura, * Kengo Kina, Tetsuo Iwagawa, and Toshiyuki Hamada Department of Chemistry
More informationA Sumanene-based Aryne, Sumanyne
A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871
More informationElectronic Supplementary Information. ligands for efficient organic light-emitting diodes (OLEDs)
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 27 Electronic Supplementary Information bis-zn II salphen complexes bearing pyridyl functionalized
More informationSignificant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes
Significant improvement of dye-sensitized solar cell performance by a slim phenothiazine based dyes Yong Hua, a Shuai Chang, b Dandan Huang, c Xuan Zhou, a Xunjin Zhu, *a,d Jianzhang Zhao, c Tao Chen,
More informationSynthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 Supporting Information Synthesis of Secondary and Tertiary Amine- Containing MFs: C-N Bond
More informationSupplemental data. Supplemental Figure 1: Alignment of potential ERRE1 and 2 in human, mouse and rat. PEPCK promoter.
1 Supplemental data A Supplemental Figure 1: Alignment of potential ERRE1 and 2 in human, mouse and rat PEPCK promoter. 2 A B C Supplemental Figure 2: Molecular structures of 4-T analogs. a-b, GSK5182
More informationSupporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and
Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and
More informationElectronic Supplementary Information
Electronic Supplementary Information General and highly active catalyst for mono and double Hiyama coupling reactions of unreactive aryl chlorides in water Dong-Hwan Lee, Ji-Young Jung, and Myung-Jong
More informationdichloropyrimidine (1.5 g, 10.1 mmol) in THF (10 ml) added at -116 C under nitrogen atmosphere.
Supporting Information Experimental The presence of atropisomerism arising from diastereoisomerism is indicated in the 13 C spectra of the relevant compounds with the second isomer being indicated with
More informationSUPPLEMENTARY INFORMATION
doi:10.1038/nature22309 Chemistry All reagents and solvents were commercially available unless otherwise noted. Analytical LC-MS was carried out using a Shimadzu LCMS-2020 with UV detection monitored between
More informationSUPPORTING INFORMATION. Fathi Elwrfalli, Yannick J. Esvan, Craig M. Robertson and Christophe Aïssa
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 SUPPORTING INFORMATION S1 Fathi Elwrfalli, Yannick J. Esvan, Craig M. Robertson and Christophe
More informationSupporting Information
Supporting Information Construction of Highly Functional α-amino itriles via a ovel Multicomponent Tandem rganocatalytic Reaction: a Facile Access to α-methylene γ-lactams Feng Pan, Jian-Ming Chen, Zhe
More informationStereoselective Synthesis of a Topologically Chiral Molecule: The Trefoil Knot
Stereoselective Synthesis of a Topologically Chiral Molecule: The Trefoil Knot Laure-Emmanuelle Perret-Aebi, Alexander von Zelewsky 1, Christiane Dietrich- Buchecker and Jean-Pierre Sauvage Bis-5,6-pinene
More informationSupporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B
Supporting Information Expeditious Construction of the DEF Ring System of Thiersinine B Masaru Enomoto and Shigefumi Kuwahara* Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural
More informationSupporting Online Material
Supporting Online Material Topology Guided Design and Syntheses of Highly Stable Mesoporous Porphyrinic Zirconium MOFs with High Surface Area. Tian-Fu Liu, a Dawei Feng, a Ying-Pin Chen, a,b Lanfang Zou,
More informationSupporting information
Supporting information The L-rhamnose Antigen: a Promising Alternative to α-gal for Cancer Immunotherapies Wenlan Chen,, Li Gu,#, Wenpeng Zhang, Edwin Motari, Li Cai, Thomas J. Styslinger, and Peng George
More informationSupporting Information for: Tuning the Binding Properties of a New Heteroditopic Salt Receptor Through Embedding in a Polymeric System
Supporting Information for: Tuning the Binding Properties of a ew Heteroditopic Salt Receptor Through Embedding in a Polymeric System Jan Romanski* and Piotr Piątek* Department of Chemistry, University
More informationSupporting Information
Electronic upplementary Material (EI) for rganic Chemistry rontiers. This journal is the Partner rganisations 0 upporting Information Convenient ynthesis of Pentafluoroethyl Thioethers via Catalytic andmeyer
More informationRed Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated
More informationSupporting Information
Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a
More informationPhotolysis for Vitamin D Formation. Supporting Information
S1 Synthesis of 1α-Hydroxyvitamin D 5 Using a Modified Two Wavelength Photolysis for Vitamin D Formation Supporting Information Robert M. Moriarty and Dragos Albinescu Spectra 1. 13 C: 3β-Acetoxy-stigmasta-5,7-diene
More informationSynthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain
rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry
More informationSUPPORTING INFORMATION
S1 SUPPORTING INFORMATION FIRST STEREOSELECTIVE SYNTHESIS OF (-)-SIPHONODIOL AND (-)-TETRAHYDROSIPHONODIOL, BIOACTIVE POLYACETYLENES FROM MARINE SPONGES Susana López,* Francisco Fernández-Trillo, Pilar
More informationSupporting Information
Supporting Information Iron-catalyzed three-component reaction: multiple C-C bond cleavages and reorganizations Peng Wang, Saihu Liao, Jian-Bo Zhu, Yong Tang* State Key Laboratory of Organometallic Chemistry,Shanghai
More informationFacile Multistep Synthesis of Isotruxene and Isotruxenone
Facile Multistep Synthesis of Isotruxene and Isotruxenone Jye-Shane Yang*, Hsin-Hau Huang, and Shih-Hsun Lin Department of Chemistry, National Taiwan University, Taipei, Taiwan 10617 jsyang@ntu.edu.tw
More information