Rhodium-Catalyzed Stereoselective Intramolecular [5 + 2] Cycloaddition of 3-Acyloxy 1,4-Enyne and Alkene
نویسندگان
چکیده
منابع مشابه
Rhodium-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 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 کاملEffect 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 کاملPalladium-catalyzed [3 + 2] intramolecular cycloaddition of alk-5-enylidenecyclopropanes.
Readily accessible alk-5-enylidenecyclopropanes undergo [3 + 2] intramolecular cycloaddition reactions upon treatment with appropriate palladium complexes. The method allows the rapid and efficient assembly of a variety of bicyclo[3.3.0]octane systems with up to three stereocenters. Preliminary theoretical calculations uncovered previously unsuspected mechanistic possibilities based on either a...
متن کاملTriptycenediols by rhodium-catalyzed [2+2+2] cycloaddition.
An efficient, modular synthesis of triptycene derivatives is presented, in which the triptycene ring system is constructed from readily available anthraquinone and alkyne starting materials. A rhodium-catalyzed alkyne cyclotrimerization reaction serves as the key step in this new method for the preparation of these useful unnatural products.
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2015
ISSN: 1523-7060,1523-7052
DOI: 10.1021/acs.orglett.5b02665