Ruthenium olefin metathesis catalysts bearing carbohydrate-based n- heterocyclic carbenes benjamin k keitz and robert h grubbs arnold and mabel beckman laboratory of chemical synthesis, division of chemistry and chemical engineering, california institute of technology, pasadena,. K c nicolaou et al reviews 4490 2005 wiley-vch verlag gmbh & co kgaa, weinheim doi: 101002/anie200500369 angew chem int ed 2005, 44, 4490 – 4527 scheme 4 ring-closing metathesis in the fashioning of the b- and c- ring carbohydrates of everninomicin a1b(a)c-ring model system (9) (nicolaou. Recently, the discovery of the rate enhancement by allyl sulfides in aqueous cross-metathesis has allowed the first examples of such a reaction on proteins this led to a new benchmark in substrate complexity for cross-metathesis and expanded the potential of olefin metathesis for other applications in chemical biology.
Abstract: this account is devoted to a discussion of synthetic applications of olefin metathesis in carbohydrate chemistry olefin metathesis has emerged as a highly promising and exciting area in the contemporary organic synthesis of carbon-carbon bonds metathetic ring-closure (rcm) of diene precursors is advancing. Chemical biology scheme 2 enyne-metathesis reactions in organic synthesis scheme 3 alkyne-metathesis reactions in organic synthesis k c nicolaou et al reviews 4492 ring-closing metathesis in the fashioning of the b- and c-ring carbohydrates of everninomicin a1b(a)c-ring model system (9) (nicolaou and. Published in this area has increased as more and more chemists are turning to cm to achieve smooth high-yielding transformations as key components of multistep selective syntheses 281 carbohydrates the application of olefin metathesis to carbohydrate chemistry has been the subject of two reviews published in. Olefin metathesis — application in the synthesis of natural products and related organic compounds key words: olefin metathesis diels-alder reaction domino process ring closure reaction terpenes carbasugars $ xwkru ring-closing metathesis in carbohydrate annulation angew chem int ed 37 (1998.
Over the past fifteen years, olefin metathesis [1-3] has been sophisticatedly used by scientists working in a variety of research fields to develop new synthetic routes, as well as a plethora of novel materials and industrial processes [4-8] the huge impact of metathesis to chemical synthesis led to the awarding of the 2005. This account is devoted to a discussion of synthetic applications of olefin metathesis in carbohydrate chemistry olefin metathesis has emerged as a highly promising and exciting area in the contemporary organic synthesis of carbon- carbon bonds metathetic ring-closure (rcm) of diene precursors is.
Monolithic disk-supported metathesis catalysts for use in combinatorial chemistry adv synth catal 2005, 347, 484-492 a fürstner reflections upon olefin metathesis in carbohydrate chemistry in: glycomimetics: modern synthetic methodologies (r roy, hrsg), acs symp ser, bd 896 american chemical society. Olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative organic reactions.
Improved ruthenium catalysts for z-selective olefin metathesis bk keitz, k endo, pr patel, mb herbert, rh grubbs j am chem soc 2012, 134, 693- 699 [pdf] [si] ruthenium olefin metathesis catalysts bearing carbohydrate- based n-heterocyclic carbenes bk keitz, rh grubbs organometallics 2010, 29. Ak chatterjee, in comprehensive organometallic chemistry iii, 2007 11062 olefin metathesis is a thermodynamically controlled reaction that has become a highly versatile synthetic method for alkene preparation acetate and silyl- protected sugars were superior to the corresponding benzyl-protected glucosides. Keyword [en] constitutional dynamic chemistry, selection, multivalent interactions , carbohydrates, quartz crystal microbalance, catalyst screening, aqueous olefin metathesis, c-h activation.
Ruthenium olefin metathesis catalysts bearing carbohydrate- catalysts has made olefin metathesis an indispensable tool in a variety of chemical shifts are reported in ppm downfield from me4si by using the residual solvent peak as an internal standard spectra were analyzed and processed using mestrenova ver. Recent advancements in stereoselective olefin metathesis using ruthenium catalysts t patrick montgomery 1, adam m johns 2, and robert h grubbs 1, 1 the arnold and mabel beckman laboratory of chemical synthesis, division of chemistry and chemical engineering, california institute of.
Olefin metathesis allows the exchange of substituents between different olefins - a transalkylidenation this reaction was first used in petroleum reformation for the synthesis of higher olefins (shell higher olefin process - shop), with nickel catalysts under high pressure and high temperatures nowadays, even polyenes with. Mechanism of the olefin metathesis reaction thomas j katz, and james mcginnis j am chem soc , 1975, 97 (6), pp 1592–1594 doi: 101021/ ja00839a063 publication date: march 1975 acs legacy archive cite this:j am chem soc 97, 6, 1592-1594 note: in lieu of an abstract, this is the article's first page click to. Figure 2 olefin metathesis reactions and their application to chemical biology (a ) ring-opening metathesis polymerization can produce highly functionalized and well-defined macromolecules, such as this carbohydrate-displaying polymer  (b) cross metathesis links two alkene fragments to create.