A convenient method to remove ruthenium byproducts from olefin metathesis reactions using polymer-bound triphenylphosphine oxide (TPPO)

Haack, KyoungLang; Ahn, Yu Mi; Georg, Gunda I.

doi:10.1007/s11030-005-2480-6

Cited by 20 publications

(11 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Even trace amounts of these organometallic complexes can lead to olefin isomerization, product decomposition and cell toxicity. Several relevant purification methods have already been explored, including the use of tris-(hydroxymethyl)phosphine, triphenylphosphine oxide, and dimethyl sulfoxide32–34. However, these procedures require multiple reagents, subsequent column chromatography, and relatively long exposure times for maximal efficacy.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of orthogonally reactive FK506 derivatives via olefin cross metathesis

Marinec

Evans

Gibbons

et al. 2009

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

Chemical inducers of dimerization (CIDs) are employed in a wide range of biological applications, to control protein localization, modulate protein-protein interactions and improve drug lifetimes. These bifunctional chemical probes are assembled from two synthetic modules, which each provide affinity for a distinct protein target. FK506 and its derivatives are often employed as modules in the syntheses of these bifunctional constructs, owing to the abundance and favorable distribution of their target, FK506-binding protein (FKBP). However, the structural complexity of FK506 necessitates multi-step syntheses and/or multiple protection-deprotection schemes prior to installation into CIDs. In this work, we describe an efficient, one-step synthesis of FK506 derivatives through a selective, microwave-accelerated, cross metathesis diversification step of the C39 terminal alkene. Using this approach, FK506 is modified with an array of functional groups, including primary amines and carboxylic acids, which make the resulting derivatives suitable for the modular assembly of CIDs. To illustrate this idea, we report the synthesis of a heterobifunctional HIV protease inhibitor.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of orthogonally reactive FK506 derivatives via olefin cross metathesis

Marinec

Evans

Gibbons

et al. 2009

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…Attempts using the method developed by Georg involving polymer-bound triphenylphosphine oxide unfortunately did not provide a product that was much cleaner than we had originally isolated. 151 Removal with activated carbon leads to the same unfavorable result. 152 The problem was finally resolved by use of Varian strong cation exchange chromatography.…”

Section: 150mentioning

confidence: 96%

Total Synthesis of (±)‐Haliclonacyclamine C

Smith

Sulikowski

2010

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

“…Several ruthenium scavengers are described in the literature, for example, P(CH 2 OH) 3 , Pb(OAc) 4 , DMSO or triphenylphosphine oxide (TPPO), polymer‐bound chelating phosphines or TPPO, functionalized mesoporous silicas, mercaptonicotinic acid, di(ethylene glycol) vinyl ether, H 2 O 2 , and silica‐based heterogeneous particles . Most of these compounds are commercially available, but none of them satisfy all of the above conditions.…”

Section: Introductionmentioning

confidence: 99%

High‐Performance Isocyanide Scavengers for Use in Low‐Waste Purification of Olefin Metathesis Products

Szczepaniak

Urbaniak²,

Wierzbicka³

et al. 2015

ChemSusChem

View full text Add to dashboard Cite

Three isocyanides containing a tertiary nitrogen atom were investigated for use as small-molecule ruthenium scavenging agents in the workup of olefin metathesis reactions. The proposed compounds are odorless, easy to obtain, and highly effective in removing metal residues, sometimes bringing the metal content below 0.0015 ppm. The most successful of the tested compounds, II, performs very well, even with challenging polar products. The performance of these scavengers is compared and contrasted with other known techniques, such as silica gel filtration and the use of self-scavenging catalysts. As a result, a new hybrid purification method is devised, which gives better results than using either a self-scavenging catalyst or a scavenger alone. Additionally, isocyanide II is shown to be a deactivating (reaction quenching) agent for olefin metathesis and superior to ethyl vinyl ether.

show abstract

A convenient method to remove ruthenium byproducts from olefin metathesis reactions using polymer-bound triphenylphosphine oxide (TPPO)

Cited by 20 publications

References 13 publications

Synthesis of orthogonally reactive FK506 derivatives via olefin cross metathesis

Synthesis of orthogonally reactive FK506 derivatives via olefin cross metathesis

Total Synthesis of (±)‐Haliclonacyclamine C

High‐Performance Isocyanide Scavengers for Use in Low‐Waste Purification of Olefin Metathesis Products

Contact Info

Product

Resources

About