40794-74-9Relevant academic research and scientific papers
Highly Z-selective metathesis homocoupling of terminal olefins
Jiang, Annie J.,Zhao, Yu,Schrock, Richard R.,Hoveyda, Amir H.
, p. 16630 - 16631 (2009)
(Chemical Equation Presented) Mo and W MonoAryloxide-Pyrrolide (MAP) olefin metathesis catalysts can couple terminal olefins to give as high as >98% Z-products in moderate to high yields with as little as 0.2% catalyst. Results are reported for 1-hexene, 1-octene, allylbenzene, allyltrimethylsilane, methyl-10-undecenoate, methyl-9-decenoate, allylB(pinacolate), allylOBenzyl, allylNHTosyl, and allylNHPh. It is proposed that high Z-selectivity is achieved because a large aryloxide only allows metallacyclobutanes to form that contain adjacent cis substituents and because isomerization of Z-product to E-product can be slow in that same steric environment.
Highly Z-selective olefins metathesis
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Page/Page column 39; 45, (2015/07/22)
The present invention relates generally to catalysts and processes for the Z-selective formation of internal olefin(s) from terminal olefin(s) via homo-metathesis reactions.
Tandem Z-Selective Cross-Metathesis/Dihydroxylation: Synthesis of anti-1,2-Diols
Dornan, Peter K.,Wickens, Zachary K.,Grubbs, Robert H.
supporting information, p. 7134 - 7138 (2015/06/16)
Abstract: A stereoselective synthesis of anti-1,2-diols has been developed using a multitasking Ru catalyst in an assisted tandem catalysis protocol. A cyclometalated Ru complex catalyzes first a Z-selective cross-metathesis of two terminal olefins, followed by a stereospecific dihydroxylation. Both steps are catalyzed by Ru, as the Ru complex is converted to a dihydroxylation catalyst upon addition of NaIO4. A variety of olefins were transformed into valuable, highly functionalized, and stereodefined molecules. Mechanistic experiments were performed to probe the nature of the oxidation step and catalyst inhibition pathways. These experiments point the way to more broadly applicable tandem catalytic transformations. Two steps with one cat.: 1,2-anti-Diols are accessible through a tandem Z-selective cross-metathesis/dihydroxylation using an assisted tandem catalysis protocol. Both steps are catalyzed by the Ru complex, and the stereocontrol of the cross-metathesis is translated through high stereospecificity in the dihydroxylation step to diastereoselectivity for the 1,2-anti-diol.
HIGHLY Z-SELECTIVE OLEFINS METATHESIS
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Page/Page column 18; 21, (2011/04/19)
The present invention relates generally to catalysts and processes for the Z-selective formation of internal olefin(s) from terminal olefin(s) via homo-metathesis reactions.
