17447-60-8Relevant articles and documents
Indium(III) Chloride-Promoted Intramolecular Addition of Allylstannanes to Alkynes
Miura, Katsukiyo,Fujisawa, Naoki,Hosomi, Akira
, p. 2427 - 2430 (2004)
In the presence of an equimolar amount of InCl3, 8-tributylstannyl-6-octen-1-ynes (allylstannanes bearing an alkynyl group) were efficiently cyclized to 2-allyl-1-methylenecyclopentanes. In contrast, catalytic use of InCl3 gave 2-all
Palladium-catalyzed diastereo- And enantioselective [3 + 2] cycloaddition of vinylcyclopropanes with azadienes: Efficient access to chiral spirocycles
Liu, Kai,Yang, Jianfeng,Li, Xiaoxun
, p. 826 - 831 (2021)
Benzofuran-derived azadienes (BDAs) have been widely used as four-atom synthons in transition-metal-mediated cycloaddition reactions, while the exploitation of their reactivity as a two-atom unit to construct spirocycles is still underdeveloped. Herein, we reported the first palladium(0)-catalyzed diastereo- and enantioselective [3 + 2] annulation of vinylcyclopropanes (VCPs) and BDAs. This transformation is featured with a broad substrate scope (31 examples), allowing for facile access to a variety of enantioenriched spirocycles bearing a quaternary stereogenic center in good yields with excellent regio-, diastereo-, and enantioselectivities (up to 93% yield, >20:1 dr, and mostly >99% ee) under mild reaction conditions. Moreover, the spirocyclic products could be efficiently converted to structurally complex tricyclo[8.3.0.01,5]-azatridecane and tricyclo[7.3.0.01,5]-azadodecane skeletons.
Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis
Chiba, Shunsuke,Li, Haoyu,Liu, Yuliang
supporting information, p. 6264 - 6267 (2021/07/02)
A protocol for anti-Markovnikov hydroarylation of alkenes with aryl halides has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light.
Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine
Banerjee, Prabal,Kumar, Pankaj,Kumar, Rakesh
supporting information, p. 6535 - 6550 (2020/06/09)
A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.