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Retrospective Theses and Dissertations

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Full-Text Articles in Organic Chemistry

Palladium-Catalyzed And Electrophilic Cyclization Approaches To Carbocycles And Heterocycles, Shilpa Arvind Worlikar Jan 2008

Palladium-Catalyzed And Electrophilic Cyclization Approaches To Carbocycles And Heterocycles, Shilpa Arvind Worlikar

Retrospective Theses and Dissertations

Palladium-catalyzed and electrophilic cyclization reactions are among the most studied in synthetic organic chemistry. However, these methodologies cannot always be generally applied to obtain good yields of a desired class of compounds. Many factors, including the reaction conditions, the nature of the ligands, and the reactivity of the involved species determine the product and the yield. This thesis describes several useful and novel palladium-catalyzed and electrophilic cyclization methodologies that have been optimized to obtain biologically and industrially useful carbocycles and heterocycles in good to excellent yields. These methods are tolerant of a number of functional groups including, a halogen moiety ...


Studies In Electrophilic Cyclization, Palladium Migration And Cationic Polymerization, Tanay Kesharwani Jan 2008

Studies In Electrophilic Cyclization, Palladium Migration And Cationic Polymerization, Tanay Kesharwani

Retrospective Theses and Dissertations

2,3-Disubstituted benzo[b]selenophenes have been prepared by the electrophilic cyclization of various 1-(1-alkynyl)-2-(methylseleno)arenes by Br2, NBS, I2, ICl, PhSeCl, PhSeBr and Hg(OAc) 2. This method tolerates a wide variety of functional groups, including alcohol, ester, nitrile, nitro and silyl groups, and proceeds under exceptionally mild reaction conditions. A cationic intermediate in the cyclization with Br2 has been isolated and studied, providing evidence for a stepwise cyclization process.


Mesoporous Silica Nanoparticles As Vehicles For Intracellular Trafficking And Controlled Release, Igor Iván Slowing Jan 2008

Mesoporous Silica Nanoparticles As Vehicles For Intracellular Trafficking And Controlled Release, Igor Iván Slowing

Retrospective Theses and Dissertations

Mesoporous silica nanoparticles (MSN) are introduced as vehicles for the intracellular delivery of a variety of molecular cargoes into living cells. The general synthesis of the material, the dependence of its uptake upon surface functionalization as well as its toxicity are investigated in the work.


Iodine And Palladium Approaches To Medicinally Interesting Heterocycles And Carbocycles, Jesse Page Waldo Jan 2008

Iodine And Palladium Approaches To Medicinally Interesting Heterocycles And Carbocycles, Jesse Page Waldo

Retrospective Theses and Dissertations

Chapter 1. A large number of functionally-substituted 2-alkyn-1-one O-methyl oximes have been cyclized under mild reaction conditions in the presence of ICl to give the corresponding 4-iodoisoxazoles in moderate to excellent yields. The resulting 4-iodoisoxazoles undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles, including valdecoxib.;Chapter 2. The iodocyclization of O-methyloximes of 2-alkyn-1-ones affords 4-iodoisoxazoles, which undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles. The palladium-catalyzed processes have been adapted to parallel synthesis utilizing commercially available boronic acid, acetylene, styrene and amine sublibraries. Accordingly, a diverse 51-member library of 3,4,5-trisubstituted isoxazoles has been generated ...


An Improved Preparation Of Levoglucosenone From Cellulose, Joseph Allan Marshall Jan 2008

An Improved Preparation Of Levoglucosenone From Cellulose, Joseph Allan Marshall

Retrospective Theses and Dissertations

Levoglucosenone (1) is produced in ca. 12% yield from cellulose. The preparation is carried out under reduced pressure and in the presence of soybean oil and 2.5% phosphoric acid based on the cellulose mass. Various factors are investigated to determine the effect they have on the yield of 1 from cellulose, and the optimized procedure is given. Levoglucosenone (1) can be made on the gram scale using this process, and the vacuum distillation of the compound results in a purity of greater than 90%. This procedure is the most convenient way to make levoglucosenone on the bench top given ...


Synthetic Approaches To Novel Highly Functionalized Polythiophenes, Michael Mitchell Jan 2007

Synthetic Approaches To Novel Highly Functionalized Polythiophenes, Michael Mitchell

Retrospective Theses and Dissertations

Regioregular poly(3-alkylthiophene), rr-P3AT, is a conducting polymer with numerous uses especially in the chemical and electrical sensor field. When combined with a coil type polymer, the new rod-coil block copolymer becomes attractive for nano-scale morphology control. However, one problem with rr-P3ATs is the difficulty associated with separating starting materials from the products. This can be limiting in their uses as block-copolymers and further functionalization of side chains. This difficult separation results in the need for high yielding reactions with side products that can be removed in methanol or hexanes. Based upon these requirements, Click chemistry seemed like an ideal ...


Synthesis Of 2(3h)-Furanones Via Electrophilic Cyclization, Ziwei W. Just Jan 2007

Synthesis Of 2(3h)-Furanones Via Electrophilic Cyclization, Ziwei W. Just

Retrospective Theses and Dissertations

The electrophilic cyclization of functionally-substituted alkynes is a very promising route to an extraordinary range of medicinally-interesting, functionally-substituted heterocycles and carbocycles. A variety of highly substituted 2(3H)-furanones are readily prepared from 3-alkynoate esters and the corresponding acids via electrophilic cyclization. This highly efficient approach proceeds under mild conditions, tolerates various functional groups, and generally provides 2(3H)-furanones in good to excellent yields. The cyclizations of 3-alkynoate esters and the corresponding acids have been performed using an excess of the electrophile at room temperature using either methylene chloride or acetonitrile as the solvent. Successful electrophiles in this process ...


Utilization Of Selected Biorenewable Resources: Solubilization Of Lignocellulosics And Conjugation Of Soybean Oil, Reed E. Oshel Jan 2007

Utilization Of Selected Biorenewable Resources: Solubilization Of Lignocellulosics And Conjugation Of Soybean Oil, Reed E. Oshel

Retrospective Theses and Dissertations

In recent years, concern has risen over the use of fossil fuels due to their contribution to global warming, and to our dependence on imports of petroleum from nations that could pose a threat to national security. As a result, it has become increasingly important to develop technologies to replace fossil fuel based products with biorenewable alternatives. In this thesis nearly quantitative solubilization of lignocellulosic materials using phosphite esters has been realized, and is presented as a potential pretreatment for production of fermentable sugars for use in manufacturing commodity chemicals, specifically ethanol. Water solubilization of lignocellulosics using phosphite esters will ...


Direct Approaches Toward Natural Product Synthesis, Aniket Mohan Thite Jan 2007

Direct Approaches Toward Natural Product Synthesis, Aniket Mohan Thite

Retrospective Theses and Dissertations

In this dissertation, we have explored direct routes to several biologically active natural products.;Chapter 1 describes a novel way to prepare benzoxepin core using a ring-closing metathesis reaction. Bauhiniastatins, which are reported to possess anti-cancer activities and contain benzoxepin skeleton, can thus be synthesized using this methodology.;Chapter 2 illustrates a short synthesis of bauhinoxepin J, which entails use of an environmentally benign radical reaction. This innovative intramolecular radical cyclization opens new avenues for constructing natural products with embeded quinone subunit. Chapter 3 depicts a direct route for the synthesis of aurones and benzophenones, which makes use of 1 ...


Titanium Dioxide Particle Size Effects On The Degradation Of Organic Molecules, Timothy Lee Hathway Jan 2007

Titanium Dioxide Particle Size Effects On The Degradation Of Organic Molecules, Timothy Lee Hathway

Retrospective Theses and Dissertations

Nanometer-size titania photocatalysts exhibit variations in chemical properties due to quantum effects on the semiconductor band gap and due to surface and crystalline properties. Degradation of organic molecules appears to be most efficient at particle sizes between 10 and 100 nm for anatase phase catalysts. This study focuses on the early chemical steps of degradation and degradation kinetics of two probe molecules, 4-methoxyresorcinol (MRC) and 1-para-anisyl-1-neopentanol (ANP) when the Millennium PC series anatase titania catalysts are used. These catalysts differ in particle size based on the amount of thermal annealing. Product formation ratios show that primary particle size does not ...


Multifunctionalized Mesoporous Silica Nanoparticles For Selective Catalysis, Hung-Ting Chen Jan 2007

Multifunctionalized Mesoporous Silica Nanoparticles For Selective Catalysis, Hung-Ting Chen

Retrospective Theses and Dissertations

The research presented and discussed within this dissertation involves the development of multifunctional mesoporous silica nanoparticles (MSN), and an investigation of performance of those MSN materials for heterogeneous catalysis.;A heterogeneous Lewis base MSN catalyst with an immobilized 4-dimethylaminopyridine functionality (DMAP-MSN) was synthesized, and have been demonstrated the catalytic activities of several nucleophilic reactions, such as acylation, silylation, and Baylis-Hillman reactions, and recyclable at least up to ten times. An unprecedented selectivity of Baylis-Hillman catalyzed by DMAP-MSN has also been observed, which could be attributed to size-discriminating effect induced by the 3-D cavity of regular mesoporous structure.;To take advantage ...


Palladium(Ii) And Platinum(Ii) Synthetic Peptidases: Residue- And Sequence-Selective Hydrolysis And The Photochemistry Of Sulfoxides, S,C-Sulfonium Ylides, And Sulfilimines: Unimolecular Bond Cleavage, Stacey Anne Stoffregen Jan 2007

Palladium(Ii) And Platinum(Ii) Synthetic Peptidases: Residue- And Sequence-Selective Hydrolysis And The Photochemistry Of Sulfoxides, S,C-Sulfonium Ylides, And Sulfilimines: Unimolecular Bond Cleavage, Stacey Anne Stoffregen

Retrospective Theses and Dissertations

In this dissertation the photochemistry of sulfoxides, sulfilimines, and S,C-sulfonium ylides was explored both computationally and experimentally. Dibenzothiophene-S-oxide has been previously shown to undergo deoxygenation to form dibenzothiophene and a reactive intermediate believed to be O(3P). In this study, the photochemistry of S,C-sulfonium ylides of thiophenes was explored and shown to result in unimolecular bond scission of the S-C ylidic bond to give the corresponding sulfide and a reactive intermediate, analogous to the chemistry of dibenzothiophene -S-oxide. Chemical trapping studies provide indirect evidence that the reactive intermediate produced upon photolysis is a carbene.;The mechanism of unimolecular ...


Palladium Migrations And Aryne Annulations, Jian Zhao Jan 2007

Palladium Migrations And Aryne Annulations, Jian Zhao

Retrospective Theses and Dissertations

No abstract provided.


Photochemistry Of Dibenzothiophene-Based Sulfilimines, Vasumathi Desikan Jan 2007

Photochemistry Of Dibenzothiophene-Based Sulfilimines, Vasumathi Desikan

Retrospective Theses and Dissertations

Azides have been the most extensively investigated precursors for the photochemical generation of nitrenes. Direct spectroscopic studies as well as indirect product studies have provided adequate evidence for the intermediacy of nitrenes, in at least some azides. On the other hand, less is known on the photochemical decomposition of sulfilimines. A systematic study of the potential of sulfilimines as nitrene precursors is undertaken in the current work. N-Benzoyl, N-acetyl, N-trifluoroacetyl, N-tosyl and N-mesyl derivatives of dibenzothiophene sulfilimine have been synthesized and analyzed for their photochemical reactivities. The extended UV-Vis absorption of the dibenzothiophene moiety allows for long wavelength photolysis and ...


Development Of Novel Fluorinated High Performance Polymers And New Biomaterials From Renewable Resources , Dejan Dragoslava Andjelković Jan 2006

Development Of Novel Fluorinated High Performance Polymers And New Biomaterials From Renewable Resources , Dejan Dragoslava Andjelković

Retrospective Theses and Dissertations

New type of high performance polymers, hexafluoroisopropylidene (HFIP)-linked benzophenone polymers, have been synthesized by the Ni(0)-catalyzed coupling polymerization of newly designed bis(aryl triflate) and bis(aryl halide) monomers. New synthetic strategy based on Ni(0)-catalyzed copolymerization has also been developed in order to prepare materials with higher molecular weight and optimized thermal and mechanical properties. The unique structural characteristics of these novel polymers make them potentially interesting candidates for gas separation applications, as well as for electrical applications, such as nonvolatile organic memory;Vegetable oils represent one of the most abundant annually renewable resources in ...


Synthetic Studies On Polycyclic Indole Alkaloids , Tao Wu Jan 2006

Synthetic Studies On Polycyclic Indole Alkaloids , Tao Wu

Retrospective Theses and Dissertations

The first part of this work details the formal total synthesis of HKI 0231B and the first total synthesis of both demethyl HKI 0231A and demethyl HKI 0231B. The formal synthesis used TBAF as a mild reagent to construct the indole. The total synthesis featured an efficient radical cyclization/oxidation step to construct the skeleton and a DDQ-mediated methoxylation reaction;The second part of this work is dedicated to the synthetic efforts towards the abeo-ergolines and the total synthesis of the abeo-ergoline analogs. In the synthetic study toward the abeo-ergolines, a reaction between 4-lithioindole and the enaminone, which was prepared ...


New Synthetic Methods For Hypericum Natural Products , Insik Jeon Jan 2006

New Synthetic Methods For Hypericum Natural Products , Insik Jeon

Retrospective Theses and Dissertations

In this dissertation, we have investigated the direct and efficient synthetic route to biologically active natural products;Chapter 1 describes a concise and efficient synthetic route to the highly funtionalized tricyclic core skeleton of papuaforin B. In the course of the synthesis, an efficient cyclization method using Na/NH3 was demonstrated. Newly developed bromination method leading to an alpha-bromoenone would serve as a handle for construction of the fused pyran ring of papuaforin B. Further efforts along this line are in progress;Chapter 2 describes the direct synthesis of 7,8-dihydroxycalamenene, which includes the successful application of allylic strain in ...


The Synthesis Of Analogs Of Tamiflu Via A [3+3] Annulation And Biological Activity Of Prunella Vulgaris , Tinopiwa Goronga Jan 2006

The Synthesis Of Analogs Of Tamiflu Via A [3+3] Annulation And Biological Activity Of Prunella Vulgaris , Tinopiwa Goronga

Retrospective Theses and Dissertations

Synthetic strategies towards obtaining natural products and their derivatives provide a wealth of research for organic chemists. The two perspectives provided utilize methodology in the development towards the synthesis of Tamiflu analogs and the isolation of active fractions from a plant extraction of Prunella vulgaris.;Amino esters, such as Tamiflu, are known to have antiviral activity. Using as [3+3] annulation, several different nitro and amino analogs of Tamiflu have been concisely synthesized. The annulation is achieved using a Horner-Wadsworth-Emmons type reagent and an alpha,beta-unsaturated aldehyde or ketone in the presence of DBU.;Prunella vulgaris is a Chinese herb ...


Synthesis Of Natural Products In Hypericum And Echinacea , Jingqiang Wei Jan 2006

Synthesis Of Natural Products In Hypericum And Echinacea , Jingqiang Wei

Retrospective Theses and Dissertations

Plants, as a huge source of medicinal agents, have played a very important role in human history. As modern medicine developed, not only many useful drugs were discovered from medicinal plants, but also many botanical supplements have benefited human health. The synthesis of biologically active natural products and their analogs has become an important tool in drug discovery and life sciences;Hypericum (St. John's wort) and Echinacea are two of the herbs most commonly used by consumers in the United States. As part of an NIH-funded Iowa Botanical Supplements Research Center, our group mainly focuses on the synthesis of ...


Synthetic Studies Toward Eurycolactone C , Young Ho Seo Jan 2006

Synthetic Studies Toward Eurycolactone C , Young Ho Seo

Retrospective Theses and Dissertations

Over the last decades, organic synthesis has played an essential role in the pharmaceutical industry. The development of synthetic methodologies and strategies allow us to access complex natural products in an efficient way and fuel the drug discovery. Chapter one describes the study of aryl triflates and aryl pivalates reactions with electrophiles and provides extensive information about the regioselectivities of the reactions. Chapter two introduces a novel method to generate 6- and 8-substituted 1-methoxynaphthalene (or alpha-naphthol). Chapter three describes synthetic studies toward eurycolactone C.


Novel Aryne Chemistry In Organic Synthesis , Zhijian Liu Jan 2006

Novel Aryne Chemistry In Organic Synthesis , Zhijian Liu

Retrospective Theses and Dissertations

Arynes are among the most intensively studied systems in chemistry. However, many aspects of the chemistry of these reactive intermediates are not well understood yet and their use as reagents in synthetic organic chemistry has been somewhat limited, due to the harsh conditions needed to generate arynes and the often uncontrolled reactivity exhibited by these species. Recently, o-silylaryl triflates, which can generate the corresponding arynes under very mild reaction conditions, have been found very useful in organic synthesis. This thesis describes several novel and useful methodologies by employing arynes, which generate from o-silylaryl triflates, in organic synthesis;An efficient, reliable ...


Synthesis Of Natural Compounds In Echinacea , Jaehoon Bae Jan 2006

Synthesis Of Natural Compounds In Echinacea , Jaehoon Bae

Retrospective Theses and Dissertations

In this dissertation, we have investigated the direct and efficient synthetic route to biologically active natural products. Chapter 1 describes the synthesis of some of the natural compounds in Echinacea. Several main constituents of the plant Echinacea have been synthesized for the first time. We have developed a direct and flexible route to amides and ketones in Echinacea. The synthesized natural products have been used for standard samples for the biological studies. Chapter 2 describes the new tandem strategy to construct bicyclic systems by a Diels-Alder/ene reaction and its application for the synthesis of Isoligularone. During this tandem reaction ...


Fluorous-Tag Assisted Solution Phase Synthesis Of Mannose And Heptomannose Oligosaccharides And Study Of Their Binding Interactions Using Carbohydrate Microarray Technology , Firoz Ali Jaipuri Jan 2006

Fluorous-Tag Assisted Solution Phase Synthesis Of Mannose And Heptomannose Oligosaccharides And Study Of Their Binding Interactions Using Carbohydrate Microarray Technology , Firoz Ali Jaipuri

Retrospective Theses and Dissertations

Oligosaccharide synthesis is one of the challenging problems in carbohydrate chemistry. Carbohydrates are found in nature but they are present in heterogeneous form and in very small quantity. Over the past few decades chemical synthesis of carbohydrates has took off because of their biological properties. Since solution phase synthesis is very long and tedious, solid-phase synthesis took carbohydrate chemist to a new level. With the advent of automated solid phase synthesis developed by Seeberger and coworkers, many complex oligosaccharides were readily available for biological studies. The major drawback of solid-phase synthesis is it uses huge amount of sugar donors in ...


Solution, Solid-Phase, And Fluorous-Phase Synthesis Of Carbohydrates And Production Of Carbohydrate Microarrays , Kwang-Seuk Ko Jan 2006

Solution, Solid-Phase, And Fluorous-Phase Synthesis Of Carbohydrates And Production Of Carbohydrate Microarrays , Kwang-Seuk Ko

Retrospective Theses and Dissertations

This dissertation focuses on two specific aspects of the chemistry of carbohydrates. The first is the solid- and fluorous-phase synthesis of oligosaccharides and their use in forming microarrays. The solid- and fluorous-phase synthesis of oligosaccharides has emerged as a powerful method for the development of improvements in terms of synthesis speed and efficiency. The advantage of solid phase synthesis can be obtained very high yields by use of excess donors, ease of purification, and synthesis automation. Moreover, there are still unsolvable matters in solid-phase synthesis of oligosaccharides, which have to use a way over excess of amount donor group in ...


Synthesis Of Tetrasubstituted Olefins And Aryl Ketones Via Carbopalladation Of Alkynes And Nitriles , Chengxiang Zhou Jan 2006

Synthesis Of Tetrasubstituted Olefins And Aryl Ketones Via Carbopalladation Of Alkynes And Nitriles , Chengxiang Zhou

Retrospective Theses and Dissertations

Palladium-catalyzed reactions are versatile methods for carbon-carbon bond formation due to their generality and ability to tolerate a wide range of important organic functional groups. Developing novel Palladium-catalyzed reactions has therefore been of great interest to synthetic chemists for years;The regio- and stereoselective synthesis of tetrasubstituted olefins is a long-pursuing challenge for synthetic chemists. A multi-component reaction route is ideal to generate various tetrasubstituted olefins in a very concise manner and should be highly desirable for applications in combinatorial chemistry. A highly efficient, regio- and stereoselective route to tetrasubstituted olefins has been developed by the Pd-catalyzed three-component reaction of ...


Chemical Separations By Distillation And Chiral High Performance Liquid Chromatography , Qiqing (Max) Zhong Jan 2006

Chemical Separations By Distillation And Chiral High Performance Liquid Chromatography , Qiqing (Max) Zhong

Retrospective Theses and Dissertations

The purpose of this research was to explore a convenient method for bulk separations of volatile fatty acid (VFA) mixtures in dilute aqueous solution, and to develop new chiral stationary phases (CSPs) for enantiomeric separations by high-performance liquid chromatography (HPLC);Direct separations of acetic, propionic, and butyric acids in dilute water solution by azeotropic distillation were demonstrated. Despite of its highest boiling point among these three acids, the butyric acid is the first acid to distill, followed by propionic acid. Over half of acetic acid still remains in the pot even when the other two acids are gone. Quantitative carbon-13 ...


Synthesis And Applications Of New Polymer Bound Catalysts , Brandon Michael Fetterly Jan 2005

Synthesis And Applications Of New Polymer Bound Catalysts , Brandon Michael Fetterly

Retrospective Theses and Dissertations

This dissertation discusses three new types of polymer bound catalysts and their applications. The first type is a polymer bound cation that is an effective spectator ion for nitrate. The nitrate ion is then free to act as a catalyst in aza and thia-Michael reactions and Strecker reactions. The second catalyst was previously reported. However, its structure was incorrectly assigned. The correctly revised structure of the polymer bound azidoproazaphosphatrane shows impressive catalytic activity in the oxa-Michael reaction. The third catalyst is a polymer bound free proazaphosphatrane. It is shown to be catalytically active in the trimerization of an isocyanate to ...


Palladium And Iodine Approaches To 1,3-Dienes, Heterocycles And Carbocycles , Xiaoxia Zhang Jan 2005

Palladium And Iodine Approaches To 1,3-Dienes, Heterocycles And Carbocycles , Xiaoxia Zhang

Retrospective Theses and Dissertations

A variety of highly-substituted 1,3-dienes and 1,3,5-trienes have been regio- and stereoselectively prepared by the palladium-catalyzed coupling of vinylic iodides, internal alkynes and organoboranes in moderate to good yields. The analogous three-component coupling of aryl halides, 1,3-dienes, and boronic acids provides a useful route to 3,6-disubstituted cyclohexenes. This method is a very concise and efficient way to synthesize these molecules, whose synthesis has previously required multi-step synthesis;A wide variety of substituted quinolines have been readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I2, Br2 and ...


New Approaches To Heterocycles And Carbocycles , Tuanli Yao Jan 2005

New Approaches To Heterocycles And Carbocycles , Tuanli Yao

Retrospective Theses and Dissertations

The electrophilic cyclization of functionally-substituted alkynes is a very promising route to an extraordinary range of medicinally interesting, functionally-substituted heterocycles and carbocycles. For instance, a variety of substituted isocoumarins and alpha-pyrones are readily prepared in excellent yields under very mild reaction conditions by the reaction of o-(Ialkynyl)benzoates and (Z)-2-alken-4-ynoates with ICl, I2, PhSeCl, p-O2NC6 H4SCl, and HI. This methodology accommodates various alkynyl esters and has been successfully extended to the synthesis of polycyclic aromatic and biaryl compounds.;Electrophilic cyclization of o-(1-alkynyl)benzamides with ICl, I2, and NBS, affords a variety of substituted isoindolin-1-ones in good to ...


Enantiomeric Chromatographic Separations And Ionic Liquids , Jie Ding Jan 2005

Enantiomeric Chromatographic Separations And Ionic Liquids , Jie Ding

Retrospective Theses and Dissertations

The chiral nature of compounds contributes to their bioactivity and their various pharmaceutical/industrial uses. As a result, the Food and Drug Administration (FDA) has implemented policies for analyzing the enantiomers of chiral compounds. Gas chromatography (GC) and liquid chromatography (LC) utilizing chiral stationary phases are the two most commonly used methods to achieve direct enantiomeric separations of chiral compounds. The first part of this dissertation includes a review of direct separation of enantiomers in gas and liquid chromatography, an example of the enantiomeric separation of various racemic sulfoxides and sulfinate esters on four derivatized cyclodextrin chiral stationary phases using ...