Organic Synthesis on Soluble Polymer Supports:  Liquid-Phase Methodologies

Gravert, Dennis J.; Janda, Kim D.

doi:10.1021/cr960064l

Cited by 630 publications

(309 citation statements)

References 125 publications

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“…Separation of the functionalized matrix is achieved by either solvent or heat precipitation, membrane filtration, or sizeexclusion chromatography. [233] A variety of successful microwave-assisted transformations involving soluble polymers such as polyethylene glycol (PEG) have been reported since 1999, [234] and most recently by Sun and co-workers using controlled open-vessel microwave conditions. [235,236] In the example shown in Scheme 49 polyethylene glycol of molecular weight 6000 (PEG 6000) was used as a support for the synthesis of a small library of thiohydantoins.…”

Section: Liquid-phase Synthesis On Soluble Polymer Supportsmentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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Section: Liquid-phase Synthesis On Soluble Polymer Supportsmentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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“…According to a recently published similar procedure, [30,31] (L)-Tyrosine is chosen as the starting material, methyl esterification and protection of amino group gave 2. Then the phenolic hydroxyl group was selectively protected using the TBS, following by reduction by LiAlH 4 and removal of the Boc-protecting group to afford the chiral amino alcohol 5 ( Figure 2). …”

Section: Resultsmentioning

confidence: 99%

“…[2,3] As soluble polymer modified poly(ethylene glycol)s (PEGs) recently emerged as readily functionalized, commercially available polymers that are soluble in some solvents and insoluble in a few other solvents for example ether and n-hexane. [4][5][6][7][8][9][10][11][12][13] Recently, the monomethyl ether of PEG (MeO-PEG) has successfully being used for supporting chiral ligands to be transformed in catalysts for some catalytic asymmetric reactions. MeO-PEG has also been employed by us for the immobilization of MeO-PEGsupported tunable axial chiral bisphosphine ligands which were applied in asymmetric hydrogenation of quinolines with up to 92% ee.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of MeO-PEG-Supported Ferrocenyloxazoline Ligands and Their Application in Asymmetric Catalysis

Liu¹,

Shi²,

Wang³

et al. 2013

Acta Chim. Sinica

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A simple synthesis of ferrocenyloxazoline derived chiral N,P ligands and N,S ligands immobilized on a MeO-PEG-support is described. The metal complexes of chiral ligands have been successfully applied to 1,3-dipolar cycloaddition reaction of azomethine ylides and asymmetric allylic substitution reaction, providing the products with up to 97% ee and 90% ee, respectively. The MeO-PEG-supported metal complex catalysts can be recycled easily and reused.

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“…Uma estratégia muito elegante foi relatada por Janda e col., que consistiu na utilização de um polímero solúvel para a preparação de coleções combinatórias 22 . O homopolímero mais comumente empregado para imobilização do substrato é o polietilenoglicol, principalmente devido à sua alta solubilidade frente a uma grande variedade de solventes orgânicos 22 .…”

Section: Síntese Em Polímeros Solúveisunclassified

Aplicações da química combinatória no desenvolvimento de fármacos

Dias¹,

Corrêa²

2001

Quím. Nova

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Recebido em 17/2/00; aceito em 28/8/00 APPLICATIONS OF COMBINATORIAL CHEMISTRY TO DRUG DEVELOPMENT. Combinatorial Chemistry has become a very efficient methodology in drug research. Recent progress in combinatorial synthesis performed both in solid and solution phase have led to a change in the paradigm for the identification and optimization of lead compounds. This article gives an overview of the principal characteristics of combinatorial libraries and some examples of the application of this methodology in the identification of test compounds and lead compound optimization, either from synthetic or natural sources.Keywords: combinatorial chemistry; drug development; small molecule libraries. Quim. Nova, Vol. 24, No. 2, 236-242, 2001. Divulgação INTRODUÇÃOO processo de desenvolvimento de fármacos incorporou profundas transformações no decorrer da última década. Com o avanço da Biologia Molecular inúmeros processos biológicos foram identificados, fornecendo assim diversos novos alvos macromoleculares passíveis de intervenção terapêutica. Paralelamente, a miniaturização e o desenvolvimento de dispositivos automatizados para a realização de ensaios biológicos automatizados (do inglês, High Throughput Screening, HTS) possibilitaram a avaliação de uma grande quantidade de substâncias frente a estes novos alvos. A resposta a esta demanda crescente por substâncias estruturalmente inovadoras para avaliação farmacológica estabeleceu um novo paradigma na busca por compostos-protótipo e na otimização/desenvolvimento dos já existentes. A preparação conjunta -na forma de misturas -ou paralela -na forma de substân-cias puras -de coleções com grande número de compostos estruturalmente relacionados, com sequências de reação semelhantes e com diversidade estrutural gerada pela introdução de blocos de construção com diferentes grupos substituintes promoveu uma grande transformação em relação aos métodos até então utilizados no planejamento de fármacos [1][2][3][4][5] . Ainda incipiente e restrita à preparação de coleções de peptídeos e nucleotídeos, a Química Combinatória apresentou um crescimento vertiginoso desde a preparação de uma coleção combinatória de benzodiazepinas em 1992, trabalho pioneiro realizado por Ellmann e col., que consistiu na primeira coleção combinatória de moléculas orgânicas pequenas 6 . A Química Combinatória extrapolou a esfera da Química Medicinal e vem sendo crescentemente utilizada nas áreas de agroquímicos, catálise homogênea e heterogênea, biocatálise, novos materiais, entre outros 1-4 . A Figura 1 apresenta a evolução do número de publicações científicas na área de Química Combinatória ao longo dos últimos anos 7 . As coleções combinatórias podem ser divididas entre as preparadas por síntese paralela, onde as etapas sintéticas são realizadas simultaneamente, mas cada composto é preparado em um compartimento de reação separadamente, e as preparadas na forma de mistura, ou seja, a um substrato é adicionado uma mistura de reagentes (building blocks), fornecendo então uma mistura de produtos. Por dem...

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Organic Synthesis on Soluble Polymer Supports: Liquid-Phase Methodologies

Cited by 630 publications

References 125 publications

Controlled Microwave Heating in Modern Organic Synthesis

Controlled Microwave Heating in Modern Organic Synthesis

Synthesis of MeO-PEG-Supported Ferrocenyloxazoline Ligands and Their Application in Asymmetric Catalysis

Aplicações da química combinatória no desenvolvimento de fármacos

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