135513-98-3Relevant academic research and scientific papers
A remarkable rate acceleration of the Baylis-Hillman reaction
Lee,Yang,Chen
, p. 1612 - 1613 (2001)
Treatment of α-naphthyl acrylate with both aliphatic and aromatic aldehydes in the presence of DABCO (30 mol%) afforded the desired (α-methylene-β-hydroxy)esters with reasonable chemical yields (51-88%) within 20 min.
An Improved Protocol for the Morita-Baylis-Hillman Reaction Allows Unprecedented Broad Synthetic Scope
Amarante, Giovanni W.,Camilo, Nilton S.,Carpanez, Arthur G.,Coelho, Fernando,Fernandes, Fábio S.,Lima, Samia R.,Rodrigues, Manoel T.,Santos, Hugo,Serafim, José Cláudio,Silva, Thiago S.,Zeoly, Lucas A.,de Oliveira, Aline S. B.
supporting information, (2022/01/22)
The Morita-Baylis-Hillman (MBH) reaction has been stablished as an important C?C bond-forming transformation between carbonyl-containing compounds and activated olefins. However, the slow reaction rate usually observed with electron-rich electrophilic par
Enantioselective Lewis base catalyzed phosphonyldifluoromethylation of allylic fluorides using a: C -silyl latent pronucleophile
Zi, You,Lange, Markus,Vilotijevic, Ivan
supporting information, p. 5689 - 5692 (2020/06/19)
The first enantioselective phosphonyldifluoromethylation is enabled by the use of diethyl (difluoro(trimethylsilyl)-methyl)phosphonate reagent as a latent pronucleophile in the Lewis base catalyzed substitution of allylic fluorides. The reaction proceeds
Unprecedented E-stereoselectivity on the sigmatropic Hurd-Claisen rearrangement of Morita-Baylis-Hillman adducts: A joint experimental-theoretical study
Silva, Vinicius Sobral,Tolentino, Terezinha Alves,Rodrigues, Tiago Costa Alves Fontoura,Santos, Fernanda Ferrari Martins,Machado, Daniel Francisco Scalabrini,Silva, Wender Alves,Oliveira, Heibbe Cristhian Benedito De,Machado, Angelo Henrique Lira
, p. 4498 - 4511 (2019/05/17)
Herein we report the first systematic investigation of the tandem mercury(ii) catalysed transvinylation/Hurd-Claisen rearrangement of MBH adducts derived from alkyl acrylates. This is the first report of E-selectivity for MBH adducts with alkyl side chain
Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbonates
Formánek, Bed?ich,?imek, Michal,Kamlar, Martin,Císa?ová, Ivana,Vesely, Jan
, p. 907 - 920 (2019/02/10)
An organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates with aromatic amines in the presence of β-isocupreidine is described. Chiral allylic amines were obtained in almost quantitative yields (90-96%) with moderate enantioselectivity. Recrystallization afforded products in good yields (45-73%) and high optical purity (82-99% ee). This method provides a facile and efficient route to obtain optically active β-lactams, including the building block of the cholesterol-lowering drug Ezetimibe.
Direct Synthesis of Dihydropyrrolo[2,1-a]Isoquinolines through FeCl3 Promoted Oxidative Aromatization
Cui, Hai-Lei,Jiang, Lu,Tan, Hao,Liu, Si
supporting information, p. 4772 - 4780 (2019/10/28)
We have developed a straightforward FeCl3 promoted synthesis of dihydropyrrolo[2,1-a]isoquinolines through formal (3+2) cycloaddition/oxidative aromatization cascade of dihydroisoquinoline with Morita-Baylis-Hillman carbonates (up to 96% yield)
Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates
Do?ekal, Vojtěch,?imek, Michal,Dra?ínsky, Martin,Vesely, Jan
supporting information, p. 13441 - 13445 (2018/09/21)
The present study reports the organocatalytic enantioselective allylic amination of Morita–Baylis–Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Br?nsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.
Radical Cascade-Triggered Controlled Ring-Opening Polymerization of Macrocyclic Monomers
Huang, Hanchu,Sun, Bohan,Huang, Yingzi,Niu, Jia
supporting information, p. 10402 - 10406 (2018/06/27)
A strategy for the controlled radical ring-opening polymerization of macrocyclic monomers is reported. Key to this approach is an allyl alkylsulfone-based ring-opening trigger that can undergo a radical cascade reaction to extrude sulfur dioxide and gener
Synthesis of Chiral α-Trifluoromethylamines with 2,2,2-Trifluoroethylamine as a "building Block"
Li, Xiaoyuan,Su, Jinhuan,Liu, Zhourujun,Zhu, Yuanyuan,Dong, Zhenghao,Qiu, Shuai,Wang, Jiayi,Lin, Li,Shen, Zhiqiang,Yan, Wenjin,Wang, Kairong,Wang, Rui
supporting information, p. 956 - 959 (2016/03/15)
The β-isocupreidine, a cinchonine derived alkaloid, catalyzed asymmetric SN2′-SN2′ reaction between N-2,2,2-trifluoroethylisatin ketimines and MBH type carbonates was realized in a simple and efficient way. A series of chiral α-trifl
Versatile O- and S-functionalized 1,2,3-triazoliums: Ionic liquids for the Baylis-Hillman reaction and ligand precursors for stable MIC-transition metal complexes
Mendoza-Espinosa, Daniel,González-Olvera, Rodrigo,Osornio, Cecilia,Negrón-Silva, Guillermo E.,Santillan, Rosa
supporting information, p. 1587 - 1591 (2015/03/18)
The efficient synthesis of O- and S-functionalized 1,2,3-triazoliums is reported. Owing to their physical properties, these cations are efficient ionic liquids for Baylis-Hillman addition under mild reaction conditions. Simultaneously, the functionalizati
