Interception of a Rautenstrauch Intermediate by Alkynes for [5+2] Cycloaddition: Rhodium-Catalyzed Cycloisomerization of 3-Acyloxy-4-ene-1,9-diynes to Bicyclo[5.3.0]decatrienes
نویسندگان
چکیده
منابع مشابه
Effect of ester on rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes.
We systematically examined the effect of different esters on the rhodium-catalyzed intermolecular [5+2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes with a concomitant 1,2-acyloxy migration. Significant rate acceleration was observed for benzoate substrates bearing an electron-donating substituent. The cycloaddition can now be conducted under much more practical conditions for most termina...
متن کاملRhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne.
A Rh-catalyzed 1,3-acyloxy migration of propargyl ester followed by intramolecular [4+2] cycloaddition of vinylallene and unactivated alkyne was developed. This tandem reaction provides access to bicyclic compounds containing a highly functionalized isotoluene or cyclohexenone structural motif, while only aromatic compounds were observed in related transition metal-catalyzed cycloadditions.
متن کاملRhodium-catalyzed 1,3-acyloxy migration and subsequent intramolecular [4+2] cycloaddition of vinylallene and unactivated alkynew
The Diels–Alder cycloaddition is arguably the most powerful reaction for the construction of substituted six-membered rings from various 2p and 4p reactants. However, unactivated 2p and 4p systems either require very harsh conditions or fail to undergo cycloadditions. In many cases, transition metal catalysts facilitated chemical transformations that were inaccessible under thermal conditions a...
متن کاملRhodium-catalyzed linear codimerization and cycloaddition of ketenes with alkynes.
A novel rhodium-catalyzed linear codimerization of alkyl phenyl ketenes with internal alkynes to dienones and a novel synthesis of furans by an unusual cycloaddition of diaryl ketenes with internal alkynes have been developed. These reactions proceed smoothly with the same rhodium catalyst, RhCl(PPh(3))(3), and are highly dependent on the structure and reactivity of the starting ketenes.
متن کاملRhodium-catalyzed [2+2+2] cycloaddition of oximes and diynes to give pyridines.
Oximes and diynes undergo efficient cycloaddition in the presence of a catalytic amount of a cationic rhodium(I)/dppf complex (see scheme). Spontaneous dehydration of the initially formed cycloadducts leads to the formation of a variety of substituted pyridines in moderate to good yields. The transformation could also be achieved in a one-pot procedure using aldehydes.
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ژورنال
عنوان ژورنال: Angewandte Chemie International Edition
سال: 2011
ISSN: 1433-7851
DOI: 10.1002/anie.201103136