1172591-49-9Relevant academic research and scientific papers
Visible-Light-Driven, Metal-Free Divergent Difunctionalization of Alkenes Using Alkyl Formates
Zheng, Ming,Hou, Jing,Zhan, Le-Wu,Huang, Yan,Chen, Ling,Hua, Li-Li,Li, Yan,Tang, Wan-Ying,Li, Bin-Dong
, p. 542 - 553 (2021/01/14)
In recent decades, difunctionalization of alkenes has received considerable attention as an efficient and straightforward way to increase molecular complexity. However, examples of the difunctionalization of alkenes initiated by the intermolecular addition of alkoxycarbonyl radicals providing substituted alkanoates are still rare. Herein, we present the visible light-driven metal-free divergent difunctionalization of alkenes triggered by the intermolecular addition of alkoxycarbonyl radicals under ambient conditions. Employing alkyl formates as precursors of alkoxycarbonyl radicals and 4CzIPN as the photocatalyst, a variety of substituted alkanoates, including β-alkoxy, β-hydroxy, β-dimethoxymethoxy, and β-formyloxy alkanoates, could be facilely accessed with high functional group tolerance and high efficiency. Moreover, the mechanism study revealed that β-hydroxy alkanoates were generated by a selective decomposition of orthoformates promoted by the N-alkoxyazinium salt.
Ar-BINMOL-derived salan-Cu(II) complex-catalyzed silyl-reformatsky reaction of aromatic aldehydes
Li, Fei,Zhou, Wei,Zheng, Long-Sheng,Li, Li,Zheng, Zhan-Jiang,Xu, Li-Wen
supporting information, p. 2861 - 2869 (2014/09/17)
In this work, we have developed a facile protocol with salan-Cu system for the facile and selective synthesis of β-hydroxyesters via silyl-Reformatsky reaction with -silylester and aldehydes. The screening and optimization of reaction conditions led to the determination of a practical and efficient procedure in which the salan-Cu exhibited promising catalytic activity in dimethylsulfoxide, in which the silyl-Reformatsky reaction of aromatic aldehydes with -trimethylsilylmethylacetate gave the corresponding β-hydroxyester derivatives in excellent yields (up to 98%) under fluoride-free reaction conditions.
Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: The influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications
Borowiecki, Pawel,Bretner, Maria
, p. 925 - 936 (2013/09/23)
Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor.
Catalysis of Mukaiyama aldol reactions by a tricyclic aluminum alkoxide Lewis acid
Raders, Steven M.,Verkade, John G.
supporting information; experimental part, p. 5417 - 5428 (2009/12/08)
(Chemical Equation Presented) The Mukayiama aldol reaction of aldehydes is efficiently accomplished with a low concentration of the dimeric alumatrane catalyst 2 at mild or subambient temperatures. Our protocol tolerates a wide variety of electron-rich, neutral, and deficient aryl, alkyl, and heterocyclic aldehydes. A wide variety of enol silyl ethers are also tolerated. An intermediate that was isolated provides mechanistic information regarding the role of dimeric 2 in the Mukaiyama aldol reaction. Experimental evidence is presented for the stronger Lewis acidity of 5 compared with F3B.
