57718-07-7Relevant articles and documents
Matsuda-Heck arylation of itaconates: A versatile approach to heterocycles from a renewable resource
Krause, Andreas,Sperlich, Eric,Schmidt, Bernd
supporting information, p. 4292 - 4302 (2021/05/31)
Itaconic acid esters and hemiesters undergo Pd-catalyzed coupling reactions with arene diazonium salts in high to excellent yields. The coupling products of ortho-nitro arene diazonium salts can be converted in one or two steps to benzazepine-2-ones.
Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization
Yang, Qi-Liang,Xing, Yi-Kang,Wang, Xiang-Yang,Ma, Hong-Xing,Weng, Xin-Jun,Yang, Xiang,Guo, Hai-Ming,Mei, Tian-Sheng
supporting information, p. 18970 - 18976 (2019/12/04)
Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording α-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.
Synthesis and Bioactivity of Polymer-Based Synthetic Mimics of Antimicrobial Peptides (SMAMPs) Made from Asymmetrically Disubstituted Itaconates
Boschert, David,Schneider-Chaabane, Alexandra,Himmelsbach, Andreas,Eickenscheidt, Alice,Lienkamp, Karen
, p. 8217 - 8227 (2018/05/30)
A series of asymmetrically disubstituted diitaconate monomers is presented. Starting from itaconic anhydride, functional groups could be placed selectively at the two nonequivalent carbonyl groups. By using 2D NMR spectroscopy, it was shown that the first functionalization step occurred at the carbonyl group in the β position to the double bond. These monomers were copolymerized with N,N-dimethylacrylamide (DMAA) to yield polymer-based synthetic mimics of antimicrobial peptides (SMAMPs). They were obtained by free radical polymerization, a metal-free process, and still maintained facial amphiphilicity at the repeat unit level. This eliminates the need for laborious metal removal and is advantageous from a regulatory and product safety perspective. The poly(diitaconate-co-DMAA) copolymers obtained were statistical to alternating, and the monomer feed ratio roughly matched that of the repeat unit content of the copolymers. Investigations of varied R group hydrophobicity, repeat unit ratio, and molecular mass on antimicrobial activity against Escherichia coli and on compatibility with human keratinocytes showed that the polymers with the longest R groups and lowest DMAA content were the most antimicrobial and hemolytic. This is in agreement with the biological activity of previously reported SMAMPs. Thus, the design concept of facial amphiphilicity has successfully been transferred, but the selectivity of these polymers for bacteria over mammalian cells still needs to be optimized.
Highly chemoselective esterification reactions and Boc/THP/TBDMS discriminating deprotections under samarium(III) catalysis
Gopinath, Pushparathinam,Nilaya, Surapaneni,Muraleedharan, Kannoth Manheri
supporting information; experimental part, p. 1932 - 1935 (2011/06/21)
The usefulness of SmCl3 as an excellent catalyst for chemoselective esterifications and selective removal of acid sensitive protecting groups such as Boc, THP, and TBDMS in the presence of one another is demonstrated through suitable examples.
An efficient and regiospecific esterification of dioic acids using PTSA
Rama Devi,Rajaram
, p. 294 - 296 (2007/10/03)
Regiospecific mono alkyl esters of dioic acids have been obtained in excellent yield using PTSA as a catalyst. This method is mild and simpler than the previous methods.
Selective enzymatic transformations of itaconic acid derivatives: An access to potentially useful building blocks
Ferraboschi, Patrizia,Casati, Silvana,Grisenti, Paride,Santaniello, Enzo
, p. 3251 - 3258 (2007/10/02)
Hydrolytic enzymes regioselectively catalyze the hydrolysis of diethyl itaconate 5a to the monoester 5c and opening of itaconic anhydride 6 to the regioisomeric monoester 5b that was transformed into the hydroxy esters 2. This was used for the synthesis of β-methylene-γ-butyrolactone 7 and of the racemic epoxyalcohol 3, that was resolved by a highly enantioselective Pseudomonas fluorescens lipase-catalyzed transesterification into (S)-3 and (S)-8 (90 and 86% ee, respectively).
