338463-00-6Relevant academic research and scientific papers
An asymmetric oxidative cyclization/Mannich-type addition cascade reaction for direct access to chiral pyrrolidin-3-ones
Zhou, Su,Xie, Xiongda,Xu, Xinxin,Dong, Shanliang,Hu, Wenhao,Xu, Xinfang
supporting information, p. 12171 - 12174 (2021/11/30)
An efficient gold and chiral phosphoric acid cooperatively catalyzed enantioselective oxidative cyclization/Mannich-type addition reaction of homopropargyl amides with nitrones has been developed, which provides chiral pyrrolidin-3-ones in high yields wit
Synthesis of Polyheterocyclic Tropones by [2 + 2 + 2 + 1] Carbonylative Cycloaddition of Triynes
Salacz, Laura,Girard, Nicolas,Blond, Ga?lle,Suffert, Jean
, p. 3915 - 3918 (2018/07/25)
A direct synthesis of tropones (2,4,6-cycloheptatrienes) from simple preorganized triynes has been elaborated. This simple rhodium-catalyzed domino strategy allows one-pot access to fully substituted tropones in a 6-6-7-5 tetracyclic core in average to hi
Reactivity of Arynes for Arene Dearomatization
Karmakar, Rajdip,Le, Anh,Xie, Peipei,Xia, Yuanzhi,Lee, Daesung
, p. 4168 - 4172 (2018/07/29)
An unprecedented aryne-mediated dearomatization reaction is described. An aryne intermediate generated from arenesulfonyl ynamide-tethered triynes and tetraynes reacts with both the π-systems of a tethered alkene and the arenesulfonyl group to generate cy
Gold-Catalyzed Formal [4 + 2] Cycloaddition of 5-(Ethynylamino)pent-2-yn-1-yl Esters to 1,2,3,5-Tetrahydrobenzo [g] quinolines
Chen, Xiaoyu,Merrett, James Theodore,Hong Chan, Philip Wai
supporting information, p. 1542 - 1545 (2018/03/23)
A synthetic method to prepare 1,2,3,5-tetrahydrobenzo[g]quinolines efficiently that relies on gold(I)-catalyzed cycloisomerization of 5-(ethynylamino)pent-2-yn-1-yl esters at room temperature under atmospheric conditions is described. The proposed reaction mechanism presents a unique instance of an in situ formed allenic ester and gold keteniminium species to undergo a formal [4 + 2] cycloaddition pathway.
Intermolecular Palladium-Catalyzed Oxidative Fluorocarbonylation of Unactivated Alkenes: Efficient Access to β-Fluorocarboxylic Esters
Qi, Xiaoxu,Yu, Feng,Chen, Pinhong,Liu, Guosheng
supporting information, p. 12692 - 12696 (2017/10/06)
A novel palladium-catalyzed intermolecular oxidative fluorocarbonylation of alkenes has been developed, in which employment of a cooperative process with electrophilic ArIF2-meidated alkenes activation and palladium-catalyzed carbonylation is c
Regio- and chemoselective n-1 acylation of indoles: Pd-catalyzed domino cyclization to afford 1,2-fused tricyclic indole scaffolds
Liu, Yongxian,Huang, Yuanqiong,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 5337 - 5340 (2015/03/30)
A concise method for the synthesis of 1,2-fused tricyclic indole scaffolds by domino cyclization involving a Pd-catalyzed Sonogashira coupling, indole cyclization, regio- and chemoselective N-1 acylation, and 1,4-Michael addition is reported. This method
Rhodium-catalyzed carbonylative [3 + 2 + 1] cycloaddition of alkyne-tethered alkylidenecyclopropanes to phenols in the presence of carbon monoxide
Kim, Seyun,Chung, Young Keun
, p. 4352 - 4355 (2015/01/09)
A novel Rh-catalyzed carbonylative [3 + 2 + 1] cycloaddition of alkyne-tethered alkylidenecyclopropanes for the facile synthesis of bicyclic phenols in high yields has been developed. The reaction tolerated carbon and heteroatoms in the tether.
Gold(I)-promoted heterocyclization of internal alkynes: A comparative study of direct metallate 5-endo-dig cyclization versus a stepwise cyclization
French, Jonathan M.,Diver, Steven T.
, p. 5569 - 5585 (2014/07/08)
With cationic gold catalysts, internal alkynes bearing both propargylic acyloxy groups and tosylamide pronucleophiles were found to cyclize to give either five- or six-membered ring nitrogen heterocycles. A wide variety of gold catalysts, counterions, and solvents were examined to elucidate their effect on product distribution. In most cases, the direct 5-endo-dig cyclization was found to be the major pathway leading to good yields of dehydropyrrolidine products. Alkyne substrates bearing additional normal alkyl substituents at the propargylic position gave dehydropiperidines as the major product. This pathway is thought to proceed by way of a 1,2- Rautenstrauch rearrangement to produce a vinyl gold(I) carbene, which undergoes conjugate addition by the nitrogen pronucleophile. Structural and electronic factors were studied in the nitrogen pronucleophile and in the migrating acyloxy group. Each was found to have a minor effect on the product ratio.
Palladium-catalyzed cyclization of bromoenynamides to tricyclic azacycles: Synthesis of trikentrin-like frameworks
Campbell, Craig D.,Greenaway, Rebecca L.,Holton, Oliver T.,Chapman, Helen A.,Anderson, Edward A.
supporting information, p. 5187 - 5189 (2014/05/06)
Palladium-catalyzed cascade cyclization of bromoenynamides equipped with an additional alkyne or ynamide substituent affords azatricyclic products. Using 5- to 7-membered ring tethers, this chemistry offers a regiospecific route to highly-functionalized azacycles. Elaboration to the trikentrin B skeleton is achieved from the arylsilane cyclization products. the Partner Organisations 2014.
Synthesis of azepine derivatives by silver-catalyzed [5+2] cycloaddition of γ-amino ketones with alkynes
Zhou, Ming-Bo,Song, Ren-Jie,Wang, Cheng-Yong,Li, Jin-Heng
, p. 10805 - 10808 (2013/10/22)
Silver forges the ring: A new and practical silver-catalyzed [5+2] cycloaddition method has been developed for the synthesis of azepines through the formation of four new chemical bonds between a γ-amino ketone and an alkyne in one step. This method provi
