Matrix Assisted Synthetic Transformations:  A Mosaic of Diverse Contributions. II. The Pattern Is Completed

Hudson, Derek

doi:10.1021/cc990046s

Cited by 72 publications

(55 citation statements)

References 169 publications

(255 reference statements)

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“…[27][28][29] Our choice for a structural vinyl ether monomer fell on the chemically inert vinyl ether 2 (MeBDVE). Ether 2 was synthesized via methylation of 1 with methyl iodide in moderate yields.…”

Section: Resultsmentioning

confidence: 99%

“…[27][28][29] Obviously, in reality interactions between the polymer and any of the other molecular species present, including solvent, occur thus rendering some supports more suitable for a particular application than others. Consequently a wide range of chemically different supports used in a range of different physical formats had to be developed to address specific performance needs.…”

Section: Abstract: Novel Non-peg Derived Polyether Resins Coined Slumentioning

confidence: 99%

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Non-PEG-Derived Polyethers as Solid Supports. 1. Synthesis, Swelling Studies, and Functionalization

et al. 2003

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Section: Resultsmentioning

confidence: 99%

Section: Abstract: Novel Non-peg Derived Polyether Resins Coined Slumentioning

confidence: 99%

Non-PEG-Derived Polyethers as Solid Supports. 1. Synthesis, Swelling Studies, and Functionalization

et al. 2003

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“…1 The hydrolysis of acetate groups on SLURPS-Ac, 5 is already a point in case which reaches completion to give alcohol 6 in ethanol/water mixture under which PS gel supports collapse and perform poorly. [3][4][5][6][7][8][9][10][11][12][13] As relevant transformations, we identified the dihydroxylation of alkenes using catalytic amounts of OsO 4 in the presence of stoichiometric oxidants, 14 a key transformation in natural product synthesis and aldoximes formation, a vital intermediate step in synthetic sequences leading to important heterocyclic cores. [15][16][17][18][19] Results and discussion:…”

Section: Introductionmentioning

confidence: 99%

Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

et al. 2007

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Novel non-PEG derived polyether resins, coined SLURPS (Superior Liquid Uptake Resins forPolymer-supported Synthesis), were studied for their performance in solid-phase synthesis. Novel amino functional resins, SLURPS-NH 2 , were prepared with a loading of up to 8.5 mmol/g and employed successfully in the solid-phase synthesis of Leu-Enkephalin. The peptide was obtained with the same 2 purity when compared to its synthesis with commercial standard poly(dimethyl acrylamide) resins.Furthermore we show loading and cleavage of aromatic carboxylic acids in excellent yield. The advantageous solvent compatibility of our support was demonstrated through the biphasic dihydroxylation of alkenes with OsO 4 in t-BuOH/water mixtures producing bound 1,2-diols and synthesis and removal of a bound oxime using ethanol/water mixtures both in excellent yields. Reactions were easily monitored by gel-phase NMR and FTIR These results show that SLURPS are very well suited for organic transformations using highly polar solvent mixtures and reagents and this at much higher loading levels than standard amphiphilic resins of similar solvent compatibility. Graphical Abstract:O OH SLURPS

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“…Another, perhaps more fundamental reason is the unequal reactivities of building blocks, which leads to non-statistically distributed product mixtures, unless the stability of the products is identical (reaction performed under thermodynamic control) or the reactivities of the building blocks employed are equal (reaction performed under kinetic control). As a result, most combinatorial syntheses are performed on solid supports [2,3] and in a format in which no more than one building block reacts with its substrate(s) in any given reaction mixture. This research note reports on a modest exercise in the realm of competitive, mixed condensation reactions leading to combinatorial libraries in a one-pot procedure.…”

Section: Introductionmentioning

confidence: 99%

Relative Reactivities of Activated Carboxylic Acids in Amide-Forming Reactions Employed for the Synthesis of Tetraphenylporphyrin Libraries

Dombi

Richert

2000

Molecules

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Abstract:Presented here is a method for rapidly testing the reactivity of carboxylic acids in amide-forming reactions. For this, a mixture of two acids, one a reference compound, and one acid whose reactivity is unknown, are coupled to an aminoacylated tetrakis(paminophenyl)porphyrin under typical peptide coupling conditions. The product distribution in the resulting library is analyzed via MALDI-TOF mass spectrometry to reveal the relative reactivity. This rapid reactivity test requires sub-nanomole quantities of acids, does not involve cleavage from a support or any potentially biasing work-up, and is automatable. Thus, it is well suited for testing building blocks for combinatorial syntheses. Further, it is demonstrated that step-wise coupling can produce near-statistically distributed libraries of porphyrins when acids of very different reactivity are employed.

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Matrix Assisted Synthetic Transformations: A Mosaic of Diverse Contributions. II. The Pattern Is Completed

Cited by 72 publications

References 169 publications

Non-PEG-Derived Polyethers as Solid Supports. 1. Synthesis, Swelling Studies, and Functionalization

Non-PEG-Derived Polyethers as Solid Supports. 1. Synthesis, Swelling Studies, and Functionalization

Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

Relative Reactivities of Activated Carboxylic Acids in Amide-Forming Reactions Employed for the Synthesis of Tetraphenylporphyrin Libraries

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