10285-80-0Relevant academic research and scientific papers
Economical, Green, and Safe Route Towards Substituted Lactones by Anodic Generation of Oxycarbonyl Radicals
Petti, Alessia,Leech, Matthew C.,Garcia, Anthony D.,Goodall, Iain C. A.,Dobbs, Adrian P.,Lam, Kevin
, p. 16115 - 16118 (2019)
A new electrochemical methodology has been developed for the generation of oxycarbonyl radicals under mild and green conditions from readily available hemioxalate salts. Mono- and multi-functionalised γ-butyrolactones were synthesised through exo-cyclisation of these oxycarbonyl radicals with an alkene, followed by the sp3–sp3 capture of the newly formed carbon-centred radical. The synthesis of functionalised valerolactone derivatives was also achieved, demonstrating the versatility of the newly developed methodology. This represents a viable synthetic route towards pharmaceutically important fragments and further demonstrates the practicality of electrosynthesis as a green and economical method to activate small organic molecules.
Combining cycloisomerization with trienamine catalysis: A regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles
Chintalapudi,Galvin,Greenaway,Anderson
, p. 693 - 696 (2016)
The synthesis of polysubstituted hexahydroindoles through trienamine-organocatalyzed cycloadditions of pyrrolidinyl dienals, prepared by palladium-catalyzed cycloisomerization, is reported. The cycloadditions of this novel class of dienals proceed with excellent levels of enantio- and diastereoselectivity, with the regioselectivity of cycloaddition with respect to the tethering ring readily tuned through design of the cycloisomerization substrate. This work culminates in the first examples of double-stereodifferentiating trienamine catalysis, where catalyst stereocontrol dominates facial selectivity in the cycloaddition, affording azacyclic products that are specifically functionalized at every position.
From acyclic to cyclic α-amino vinylphosphonates by using ring-closing metathesis
Adler, Pauline,Fadel, Antoine,Prunet, Jo?lle,Rabasso, Nicolas
, p. 387 - 395 (2017)
Acyclic α-amino vinylphosphonates were alkylated through the Mitsunobu reaction then diolefinic compounds hence formed were subjected to RCM. Studies on the scope and limitations of RCM with these sterically hindered α-amino vinylphosphonates are detailed
Synergistic effect of the TiCl4/p-TsOH promoter system on the aza-Prins cyclization
Durel, Vianney,Lalli, Claudia,Roisnel, Thierry,Weghe, Pierre Van De
, p. 849 - 859 (2016)
A novel aza-Prins cyclization promoted by a synergistic combination between a Lewis acid and a Br?nsted acid to efficiently afford piperidines is described. Contrary to what has been previously reported in the literature, the generality of the reaction employing N-alkyl, N-aryl, and nonprotected homoallylamines has been demonstrated. The reaction is highly diastereoselective depending on the homoallylic amine used, N-PMP homoallyl amine leading preferentially to the trans diastereomer, and free homoallylamine affording the deprotected piperidine as single cis diastereomer.
[5+2] Cycloaddition of 2-(2-Aminoethyl)oxiranes with Alkynes via Epoxide Ring-Opening: A Facile Access to Azepines
Hu, Chao,Song, Ren-Jie,Hu, Ming,Yang, Yuan,Li, Jin-Heng,Luo, Shenglian
, p. 10423 - 10426 (2016)
A new FeCl3and BF3?OEt2co-catalyzed tandem hetero-[5+2] cycloaddition of 2-(2-aminoethyl)oxiranes with a wide range of alkynes, including terminal alkynes and alkyl-substituted internal alkynes is presented. This is the fi
Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles
Go, Takashi,Morimatsu, Akane,Wasada, Hiroaki,Tanabe, Genzoh,Muraoka, Osamu,Sawada, Yoshiharu,Yoshimatsu, Mitsuhiro
, p. 2722 - 2729 (2018)
A unique 1,7-S- and Se-shift reaction under Pummerer reaction conditions of 4-alkenyl-3-sulfinyl- and seleninylpyrroles was described. The usual Pummerer reaction of 4-(alkenylaminomethyl)-3-phenylsulfinylpyrroles and a successive reaction with tetrabutyl
Nickel/Photoredox Dual Catalytic Cross-Coupling of Alkyl and Amidyl Radicals to Construct C(sp3)-N Bonds
Zhou, Shaofang,Lv, Kang,Fu, Rui,Zhu, Changlei,Bao, Xiaoguang
, p. 5026 - 5034 (2021/05/07)
The construction of C(sp3)-N bonds via direct radical-radical cross-coupling under benign conditions is a desirable but challenging approach. Herein, the cross-coupling of alkyl and amidyl radicals to build aliphatic C-N bonds in a concise, mild, and oxid
Copper-Catalyzed Carbonylative Synthesis of β-Homoprolines from N-Fluoro-sulfonamides
Wu, Xiao-Feng,Yin, Zhiping,Zhang, Youcan
supporting information, p. 1889 - 1893 (2020/03/24)
A new methodology for the carbonylative transformation of N-fluoro-sulfonamides into N-sulfonyl-β-homoproline esters has been described. In the presence of a catalytic amount of Cu(OTf)2, a range of β-homoproline derivatives were prepared in moderate to good yield. The reaction proceeds via the intramolecular cyclization and intermolecular carbonylation of a free carbon radical. Notably, this procedure offers the possibility to build potential functionalized bioactive molecules.
Transition-Metal-Free One-Step Synthesis of Ynamides
Zeng, Xianzhu,Tu, Yongliang,Zhang, Zhenming,You, Changming,Wu, Jiao,Ye, Zhiying,Zhao, Junfeng
, p. 4458 - 4466 (2019/03/26)
A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.
Interruption of Formal Schmidt Rearrangement/Hosomi-Sakurai Reaction of Vinyl Azides with Allyl/Propargylsilanes
Fang, Guichun,Liu, Zhenhua,Cao, Shanshan,Yuan, Haiyan,Zhang, Jingping,Pan, Ling
, p. 7113 - 7116 (2018/11/23)
An interrupted Schmidt rearrangement/Hosomi-Sakurai reaction of N-tosyl and S-substituted vinyl azides is reported. With BF3·Et2O as a Lewis acid promoter, the denitrogenative fragmentation of vinyl azides facilitates the generation of the N/S-stabilized carbocations, which further undergo nucleophilic addition by allyl/propargylsilanes for C-C bond formation. As a result, a variety of homoallylic/allenylic amines can be afforded in good yields under mild reaction conditions with well-defined functional-group tolerance.
