88039-47-8Relevant academic research and scientific papers
Charge tags for most comprehensive ESI-MS monitoring of Morita-Baylis-Hillman (MBH)/aza-MBH reactions: Solid mechanistic view and the dualistic role of the charge tagged acrylate
Galaverna, Renan,Camilo, Nilton S.,Godoi, Marla N.,Coelho, Fernando,Eberlin, Marcos N.
, p. 1089 - 1098 (2016)
Neutral and charge tagged reagents were used to investigate the mechanism of the classical Morita-Baylis-Hillman (MBH) reaction as well as its aza-version using mass spectrometry with electrospray ionization (ESI-MS). The use of an acrylate (activated alk
Pro-apoptotic peptide amphiphile self-assembled with the assistance of polycations
Ikeda, Masato,Kawakami, Maika,Kitade, Yukio
, p. 1137 - 1139 (2015)
Herein, we describe how a peptide amphiphile, consisting of a pro-apoptotic peptide and a hydrophobic tail connected by a reduction-responsive cleavable spacer, forms self-assembled nanostructures. In the presence of polycations, this amphiphile exhibits
Accelerating the optimization of enzyme-catalyzed synthesis conditionsviamachine learning and reactivity descriptors
Liang, Jinhu,Liu, Dongchang,Wan, Zhongyu,Wang, Quan-De
supporting information, p. 6267 - 6273 (2021/07/28)
Enzyme-catalyzed synthesis reactions are of crucial importance for a wide range of applications. An accurate and rapid selection of optimal synthesis conditions is crucial and challenging for both human knowledge and computer predictions. In this work, a
Ligand-Dependent Regiodivergent Enantioselective Allylic Alkylations of α-Trifluoromethylated Ketones
Zhu, Yi,Ni, Yifan,Lu, Chenxi,Wang, Xiaochen,Wang, Yi,Xue, Xiao-Song,Pan, Yi
supporting information, p. 2443 - 2448 (2021/04/05)
The asymmetric introduction of the CF3 unit is a powerful tool for modifying pharmacokinetic properties and slowing metabolic degradation in medicinal chemistry. A catalytic and enantioselective addition of α-CF3 enolates allows for expeditious access to
Silver/palladium relay catalyzed 1,3-dipole annulation/allylation reactions to access fully substituted allyl imidazolidines
Han, Ruiping,Ding, Yue,Jin, Xueke,Li, Er-Qing
supporting information, p. 646 - 649 (2020/02/11)
A silver/palladium relay catalyzed 1,3-dipole annulation/allylation reaction of iminoesters and Baylis-Hillman acetates for the construction of fully substituted allyl imidazolidines is reported. The reaction of both iminoesters and Baylis-Hillman acetate
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
A Hydrazine Insertion Route to N′-Alkyl Benzohydrazides by an Unexpected Carbon-Carbon Bond Cleavage
Jha, Ajit Kumar,Kumari, Rajkiran,Easwar, Srinivasan
supporting information, p. 8191 - 8195 (2019/10/16)
A serendipitous carbon-carbon bond cleavage in the reaction of benzoyl acrylates, derived from Morita-Baylis-Hillman adducts, with hydrazines delivered new N′,N′-disubstituted benzohydrazides. The reaction features a regioselective formation of two carbon
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)
On the tandem Morita-Baylis-Hillman/transesterification processes. Mechanistic insights for the role of protic solvents
Carpanez, Arthur G.,Coelho, Fernando,Amarante, Giovanni W.
, p. 83 - 91 (2017/10/24)
Despite the remarkable rate acceleration under protic solvents such as alcohols and water, the use of acrylates as activated alkenes places a problem due to the possibility of ester hydrolysis or transesterification. Therefore, the tandem transesterification/Morita-Baylis-Hillman (MBH) reactions were investigated by ESI(+)-MS/(MS) and 1H NMR techniques. For the first time, the MBH back-reaction was fully examined by ESI(+)-MS/(MS) using labelling reagents revealed the complex equilibrium involving the Michael-type addition step of DABCO to acrylate. C- and O-protonation were observed at this stage, showing the transesterification process occurs previous to the aldol step, which is the rate-determining step of the mechanism. At this stage, a short-lived tetrahedral intermediate might be involved and should be considered in these processes.
