229028-01-7Relevant academic research and scientific papers
Au(I)/(R)-BINOL-Ti(IV) concerted catalyzed asymmetric cascade cycloaddition reaction of arylalkynols
Wang, Hongkai,Zeng, Tianlong,Chang, Weixing,Liu, Lingyan,Li, Jing
supporting information, p. 3573 - 3577 (2021/05/31)
An efficient catalytic asymmetric cascade cycloaddition reaction of arylalkynols with dioxopyrrolidines was developed. This reaction was achieved using Au(I) and (R)-BINOL-Ti(IV) bimetallic catalysts and exclusively delivered a series of chiral oxo-bridged bicyclic benzooxacine compounds in up to 86% yield with 96% ee as well as >33:1 dr. Meanwhile, three new σ bonds and three new stereogenic centers were formed in a one-pot process.
Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles
Chang, Weixing,Kong, Jingyang,Li, Jing,Liu, Lingyan,Wang, Hongkai,Zeng, Tianlong
supporting information, p. 4024 - 4032 (2021/07/12)
Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).
Synthesis of phthalan derivatives via a formal intramolecular 1,3-insertion of rhodium(II) azavinyl carbenes into O[sbnd]Si bond
Deng, Changchang,Duan, Shengguo,Jie, Yuchen,Luo, Huan,Xiang, Qiaoyi,Xu, Ze-Feng
supporting information, (2021/08/30)
The first formal intramolecular 1,3-insertion into O[sbnd]Si bond of rhodium(II) azavinyl carbene have been developed, and valuable phthalan derivatives could be synthesized efficiently. In addition, various functional groups could be introduced to the pr
The Divergent Cascade Reactions of Arylalkynols with Homopropargylic Amines or Electron-Deficient Olefins: Access to the Spiro-Isobenzofuran- b-pyrroloquinolines or Bridged-Isobenzofuran Polycycles
Wang, Lun,Liu, Lingyan,Chang, Weixing,Li, Jing
supporting information, p. 7799 - 7813 (2018/06/18)
Two divergent cascade reactions of arylalkynols with homopropargylic amines or electron-deficient olefins were developed to synthesize the spiro-isobenzofuran-b-pyrroloquinolines or bridged-isobenzofuran heterocycles in good yields, respectively. One reaction actually involved intramolecular 5-endo-dig hydroamination cyclization-protonation of homopropargylic amines to give cycloiminium ions and intramolecular 5-exo-dig hydroalkoxylation cyclization of arylalkynols to generate isobenzofuran with exocyclic double bond, followed by the nontypical Povarov-type reaction in the presence of PtCl2/FeCl3 cocatalysts. The other underwent intramolecular hydroalkoxylation cycloisomerization of alkynols with the subsequent normal [4 + 2] cycoaddition with dienophiles. Herein, the arylalkynols acted as both "masked" electron-rich olefins and "masked" electron-rich dienes.
A new and facile approach to 1,2-dihydroisoquinolin-3(4: H)-imines by the Cu(i)-catalyzed reaction of 2-ethynylbenzyl methanesulfonates, sulfonyl azides and amines
Huang, Ying,Yi, Weiyin,Sun, Qihui,Zhang, Lirong,Yi, Fengping
, p. 74 - 79 (2018/01/17)
A new, step-economical and operationally simple access to unsubstituted 1,2-dihydroisoquinolin-3(4H)-imines by Cu-catalyzed MCRs under mild conditions is described. In addition, selective hydrolysis of imines to the corresponding 1,2-dihydroisoquinolin-3(4H)-ones under refluxed conc. HCl has also been investigated.
Direct access to enantioenriched spiroacetals through asymmetric relay catalytic three-component reaction
Wu, Hua,He, Yu-Ping,Gong, Liu-Zhu
supporting information, p. 460 - 463 (2013/04/11)
The gold(I)/chiral Br?nsted acid relay catalysis enabled a highly stereoselective three-component reaction of salicylaldehydes, anilines, and alkynols to give aromatic spiroacetals in high yields and stereoselectivities.
Coupling reactions of ortho-substituted halobenzenes with alkynes. The synthesis of phenylacetylenes and symmetrical or unsymmetrical 1,2-diphenylacetylenes
Stara, Irena G.,Stary, Ivo,Kollarovic, Adrian,Teply, Filip,Saman, David,Fiedler, Pavel
, p. 649 - 672 (2007/10/03)
The Pd- or Pd/Cu-catalyzed coupling reactions of halobenzenes bearing the methyl, hydroxymethyl, acetoxymethyl, methoxycarbonyl, or both methoxy and 4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl groups in the ortho-position with gaseous or metallated acetylene, (trialkylsilyl)acetylenes, and arylacetylenes have been systematically studied. Various functionalized aryl- or diarylacetylenes have been synthesized in good to excellent yields. Whereas additional fluoro, nitro, or methoxy group attached to the benzene ring does not interfere in the coupling reactions, the presence of a methoxycarbonyl requires a careful optimization of reaction conditions to achieve moderate yields.
