119817-55-9Relevant academic research and scientific papers
Solid-phase synthesis of beta-lactams via the ester enolate-imine condensation route.
Schunk,Enders
, p. 907 - 910 (2000)
The ester enolate-imine condensation route to beta-lactams via an immobilized ester enolate has been achieved for the first time. The key reaction in the synthesis is the cyclization of the resin bound ester dianion and an imine. Traceless cleavage from the T1-triazene linker system yields the desired beta-lactams.
Well-Defined, Versatile and Recyclable Half-Sandwich Nickelacarborane Catalyst for Selective Carbene-Transfer Reactions
Wang, Linghua,Perveen, Saima,Ouyang, Yizhao,Zhang, Shuai,Jiao, Jiao,He, Gang,Nie, Yong,Li, Pengfei
supporting information, p. 5754 - 5760 (2021/03/08)
Catalytic carbene-transfer reactions constitute a class of highly useful transformations in organic synthesis. Although catalysts based on a range of transition-metals have been reported, the readily accessible nickel(II)-based complexes have been rarely used. Herein, an air-stable nickel(II)-carborane complex is reported as a well-defined, versatile and recyclable catalyst for selective carbene transfer reactions with low catalyst loading under mild conditions. This catalyst is effective for several types of reactions including diastereoselective cyclopropanation, epoxidation, selective X?H insertions (X = C, N, O, S, Si), particularly for the unprotected substrates. This represents a rare example of carborane ligands in base metal catalysis.
Blue light-promoted N–H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates: Synthesis of unnatural α-aryl amino acid derivatives
Okada, Celso Y.,dos Santos, Caio Y.,Jurberg, Igor D.
, (2020/07/03)
A photochemical protocol using blue light allows the N–H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates to afford the corresponding α-amino esters. This method is experimentally simple, inexpensive and tolerates numerous functional groups, thus allowing the straightforward preparation of a variety of α-aryl amino acid derivatives in good yields.
Identification of 1,5,7-Triazabicyclododecene and Polystyrene-Supported Superbases as Efficient Hydroxylaminolysis Agents of Sterically Hindered and Epimerizable Esters
Pierre, Romain,Gaigne, Frédéric,El-Bazbouz, Ghizlane,Mouis, Grégoire,Ouvry, Gilles,Tomas, Loic,Harris, Craig S.
supporting information, p. 1102 - 1106 (2018/04/24)
In modern pharmaceutical research, the need for reliable protocols for the preparation of chemical libraries in a controlled manner is quintessential to driving the Design-Make-Test cycle in drug discovery programs. In this letter, we communicate the iden
Visible-Light-Driven Oxidation of N -Alkylamides to Imides Using Oxone/H 2 O and Catalytic KBr
Mei, Chong,Hu, Yixin,Lu, Wenjun
supporting information, p. 2999 - 3005 (2018/05/25)
Imides are prepared conveniently by visible-light-driven oxidations of various N -alkylamides under mild conditions. The majority of the reactions proceed efficiently by using Oxone as the oxidant in the presence of a catalytic amount of KBr in H 2 O/CH 2 Cl 2 under irradiation by an 8 W white LED at room temperature. Experimental studies suggest that an imine, obtained from the substrate amide via a radical process, is the key intermediate.
N—H Insertion Reactions Catalyzed by a Dirhodium Metal-Organic Cage: A Facile and Recyclable Approach for C—N Bond Formation
Kang, Jian,Chen, Lianfen,Cui, Hao,Zhang, Li,Su, Cheng-Yong
, p. 964 - 968 (2017/06/27)
A heterogeneous metal-organic cage based on Rh-Rh bonds [Rh4(pbeddb)4(H2O)2(DMAC)2] (MOC-18; pbeddb2? = 3,3'-(1,3-phenylenebis(ethyne-2,1-diyl))dibenzoate) was applied to the N—H insertion
A novel method for synthesizing N-alkoxycarbonyl aryl α-imino esters and their applications in enantioselective transformations
Qian, Yu,Jing, Changcheng,Zhai, Changwei,Hu, Wen-Hao
, p. 301 - 307 (2012/04/04)
A new strategy for the synthesis of N-alkoxycarbonyl aryl α-imino esters in the presence of dirhodium tetraacetate [Rh2(OAc) 4] is reported to produce the desired compounds in high yield (up to 96%) under mild reaction conditions. The application of the synthetic method is demonstrated in enantioselective reduction and Friedel-Crafts reaction of indoles to afford the corresponding chiral arylglycines and indole derivatives, respectively, in high yield and excellent ee. Copyright
Chiral 1,2,4-triazoles: stereoselective acylation and chlorination
Katritzky, Alan R.,Fedoseyenko, Dmytro,Kim, Myong S.,Steel, Peter J.
experimental part, p. 51 - 57 (2010/04/24)
Acyl groups are transferred from diverse N- and O-acyl derivatives of chiral 3,5-bis-(1-hydroxyethyl)-[1,2,4]-triazole to amino acid esters enantioselectively, with 7% to 68% ee, depending on the temperature conditions and nature of the reagents. Thionyl
Enantioselective benzoylation of α-amino esters using (S)-1-benzoyl-2-(α-acetoxyethyl)benzimidazole, a chiral benzimidazolide
Karnik, Anil V.,Kamath, Suchitra S.
, p. 7435 - 7438 (2008/02/11)
(Chemical Equation Presented) A new chiral benzimidazolide is developed as a nonenzymatic acylating agent for enantioselective benzoylation of racemic α-amino esters. The process is highly efficient, which exhibits uniformly high enantioselectivity for α-amino esters with or without aryl substituents under mild reaction conditions. The chiral benzimidazolide is inexpensive and is easily accessible.
PS-IIDQ: An efficient polymer-supported amide coupling reagent
Valeur, Eric,Bradley, Mark
, p. 1164 - 1166 (2007/10/03)
Polystyrene-IIDQ is a polymer-supported coupling reagent that couples carboxylic acids to amines in good yields and high purity without the requirement of a pre-activation step. Importantly the order of addition of the amine, acid or coupling agent makes no difference to the efficiency of the coupling reaction and the reagent can be readily regenerated. The Royal Society of Chemistry 2005.
