141964-52-5Relevant academic research and scientific papers
Photochemically immobilized 4-methylbenzoyl cellulose as a powerful chiral stationary phase for enantioselective chromatography
Francotte, Eric,Huynh, Dan,Zhang, Tong
, (2016/12/30)
A process to immobilize para-methylbenzoyl cellulose (PMBC) on silica gel has been developed and applied to prepare chiral stationary phases (CSPs) for enantioselective chromatography. The immobilization was achieved by simple irradiation of the polysaccharide derivative with ultraviolet light after coating on a silica gel support. The influence of parameters such as irradiation time and solvent on immobilization effectiveness were investigated. The performance of the prepared immobilized phases were evaluated by injection of a series of racemic compounds onto the packed columns and determination of their chiral recognition ability. By contrast to the classical coated phase, the immobilized CSP can be used under various chromatographic conditions without limitation of organic solvent types as the mobile phase. This extended applicability permits to improve selectivity and to resolve chiral compounds which are not or only poorly soluble in the mobile phases which are compatible with the non-immobilized PMBC stationary phase.
From ketones to esters by a Cu-catalyzed highly selective C(CO)-C(alkyl) bond cleavage: Aerobic oxidation and oxygenation with air
Huang, Xiaoqiang,Li, Xinyao,Zou, Miancheng,Song, Song,Tang, Conghui,Yuan, Yizhi,Jiao, Ning
supporting information, p. 14858 - 14865 (2014/12/11)
The Cu-catalyzed aerobic oxidative esterification of simple ketones via C-C bond cleavage has been developed. Varieties of common ketones, even inactive aryl long-chain alkyl ketones, are selectively converted into esters. The reaction tolerates a wide range of alcohols, including primary and secondary alcohols, chiral alcohols with retention of the configuration, electron-deficient phenols, as well as various natural alcohols. The usage of inexpensive copper catalyst, broad substrate scope, and neutral and open air conditions make this protocol very practical. 18O labeling experiments reveal that oxygenation occurs during this transformation. Preliminary mechanism studies indicate that two novel pathways are mainly involved in this process. (Chemical Equation Presented)
Convenient method for the preparation of carboxylic esters using (chloromethylene)dimethylammonium chloride
Nagao, Hitoshi,Michida, Makoto,Mukaiyama, Teruaki
, p. 3208 - 3214 (2008/12/22)
(Chloromethylene)dimethylammonium chloride (Vilsmeier reagent) works as an efficient condensation reagent in the formation of carboxylic esters from carboxylic acids and alcohols under mild conditions in a one-pot procedure. Secondary alcohols are convert
SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one
Bull, Steven D.,Davies, Stephen G.,Garner, A. Christopher,Kruchinin, Dennis,Key, Min-Suk,Roberts, Paul M.,Savory, Edward D.,Smith, Andrew D.,Thomson, James E.
, p. 2945 - 2964 (2008/02/09)
The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions. The Royal Society of Chemistry 2006.
New optical resolution method based on the formation of a solid solution. Optical resolution of racemic 1-(4-methylthiophenyl)-2-phenylpropan-1-one by co-crystallization with (+)-1-(4-methoxyphenyl)-2-phenylpropan-1-one
Garcia,Collet
, p. 361 - 364 (2007/10/02)
Crystallization of ketone S-(+)-1 in the presence of a small amount of it sulfur analogue (±)-2 afforded a solid solution containing 8% of S-(+)-2; the latter was isolated in enantiomerically pure form by column chromatography. This simple optical resolut
