GRUBBS Olefin Metathesis

Hydroxylation of the terminal double bond in 140 followed by the esterification paved the way to phosphodiester 141, whereas Grubbs olefin metathesis followed by hydroxylation and esterification led to divalent phosphodiester 142. 

Subsequently, alternative syntheses of sulfoximine-containing heterocycles were studied, and one such approach was based on Grubbs olefin metathesis reaction. Using the ruthenium carbene complex 39 as catalyst, a wide range of... 

R.H. Grubbs, Olefin-Metathesis Catalysts for the Preparation of Molecules and Materials, Angew. Chem. Int. Ed. 45, 3760-3765 (2006) [Nobel Lecture],... 

Natural product synthesis and medicinal chemistry exist in a symbiotic relationship with the development of synthesis methodology. Noy-ori s asymmetric hydrogenations, Sharpless olefin oxidations, Grubbs olefin metathesis, Buchwald-Hartwig couplings and Jacobsen s hydrolytic kinetic resolution are illustrious examples with many practical applications. The key to the success of the above-mentioned reactions is that they have provided reliable shortcuts to more traditional synthetic... 

XV. Both the first and second generation Grubbs olefin metathesis catalysts have been shown to isomerize allylic ethers to vinyl ethers that are readily hydrolyzed.It is a decomposition product of the catalyst that was shown to be the isomerization catalyst. ... 

BTF can be used for some important transition metal catalyzed reactions, such as the Grubbs olefin-metathesis reaction [64] (11.1), the Petasis olefination [65]... 

A particularly useful general method for the synthesis of saturated nitrogen- and oxygen-containing partially unsaturated heterocycles, from 5-membered to medium ring-sized, is the Grubbs olefin metathesis applied, for example, to acyclic diaUcenyl-amines, as illustrated by syntheses of a dihydropyrrole and a tetrahydropyridine. ... 

Second generation Grubbs olefin metathesis catalyst... 

Minenkov Y, Occhipinti G, HeyndrickxW, Jensen VR. The Nature of the Barrier to Phosphane Dissociation from Grubbs Olefin Metathesis Catalysts. Eur J Inorg Chem. 2012 (9) 1507-1516. 

On treatment with a Grubbs olefin metathesis catalyst, the compound shown reacted with styrene to give a 95% yield of a product with the molecular formula C25H30O3, which was later used in the synthesis of a metabolite isolated from a species of mollusk. Suggest a reasonable structure for the metathesis product. 

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