6212-77-7Relevant articles and documents
Studies related to the total synthesis of the sesquiterpene core of the pyrrolobenzoxazine natural products CJ-12662 and CJ-12663
Commandeur, Ma?gorzata,Commandeur, Claude,Paolis, Michael De,Edmunds, Andrew J.F.,Maienfisch, Peter,Ghosez, Léon
, p. 3359 - 3362 (2009)
A highly effective procedure is reported to synthesize a substituted bicyclo[4.2.0]octenol derivative by regioselective cycloaddition of phenyl-1-propynyl sulfide with cyclohexenone followed by selective reduction of the ketone group and reductive elimina
Divergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor–Acceptor Cyclopropanes
Racine, Sophie,Hegedüs, Bence,Scopelliti, Rosario,Waser, Jér?me
supporting information, p. 11997 - 12001 (2016/08/16)
Efficient methods for the convergent synthesis of (poly)cyclic scaffolds are urgently needed in synthetic and medicinal chemistry. Herein, we describe new annulation reactions of thioalkynes with phthalimide-substituted donor–acceptor cyclopropanes, which gave access to highly substituted cyclopentenes and polycyclic ring systems. With silyl-thioalkynes, the Lewis acid catalyzed [3+2] annulation reaction with donor–acceptor cyclopropanes took place to afford 1-thio-cyclopenten-3-amines. On the other hand, an unprecedented polycyclic compound was formed with alkyl-thioalkynes through a reaction pathway directly involving the phthalimide group. The two transformations proceeded in good yields and tolerated a large variety of functional groups.
Mechanism and stereochemistry of domino reaction of 2,3-dichloroprop-1-ene with diphenyl dichalcogenides in the system hydrazine hydrate - KOH
Levanova,Vakhrina,Grabel'Nykh,Rozentsveig,Russavskaya,Albanov,Korchevin
, p. 1722 - 1727 (2015/05/20)
A new scheme of the domino reactions of diphenyl dichalcogenides with 2,3-dichloroprop-1-ene in the system hydrazine hydrate - KOH was suggested, which included nucleophilic substitution of the allylic chlorine atom in dichloropropene, dehydrochlorination of the product obtained with the formation of an allene derivative, addition of a nucleophile to the allene system, allene-acetylene rearrangement, addition of a nucleophile to the triple bond with the formation of a Z-adduct, isomerization of a 2,3-dichalcogenide product to Z-1,2-dichalcogenylprop-1-enes, and isomerization of Z-adducts to E-isomers. The most plausible mechanisms of individual steps, involving carbanions stabilized by the α-chalcogen atom, were considered.