5219-12-5Relevant articles and documents
Synthetic Scope of Br?nsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate
Rahaman, Mizzanoor,Ali, M. Shahnawaz,Jahan, Khorshada,Hinz, Damon,Belayet, Jawad Bin,Majinski, Ryan,Hossain, M. Mahmun
, p. 6138 - 6147 (2021/05/06)
The comprehensive study of the reactions of carbonyl compounds and ethyl diazoacetate in the presence of a Br?nsted acid catalyst is described. In result, a broad range of 3-oxo-esters were synthesized from a variety of ketones and aliphatic aldehydes by 1,2-aryl/alkyl/hydride shift. Aryl-methyl ketones produced only aryl-migrated products, whereas other ketones yielded a mixture of products. For diaryl ketones, the identity of two inseparable migrated products was confirmed by two-dimensional NMR spectroscopy.
One-Pot Reaction of Carboxylic Acids and Ynol Ethers for the Synthesis of β-Keto Esters
Zeng, Linwei,Lai, Zhencheng,Cui, Sunliang
, p. 14834 - 14841 (2018/12/14)
An one-pot reaction of carboxylic acids and ynol ethers for the synthesis of β-keto esters has been developed. Under promotion of Ag2O, various carboxylic acids and ynol ethers could transform to α-acyloxy enol esters, which undergo a following DMAP-catalyzed rearrangement to deliver β-keto esters rapidly. This method provides a direct approach to β-keto esters from carboxylic acids without any preactivation. The protocol features mild reaction conditions, broad substrate scope, and the products could be transformed to an array of compounds.
Palladium-catalyzed Cross-coupling of aryl iodides with β-trimethylsiloxy-α-diazoesters: A novel approach toward β-keto-α-arylesters
Shu, Zhibin,Zhang, Ji,Zhang, Yan,Wang, Jianbo
supporting information; experimental part, p. 1009 - 1011 (2011/12/05)
Palladium-catalyzed cross-coupling of β-trimethylsiloxy- α-diazoesters with aryl iodides provides a new approach to β-keto-α-arylesters. It is shown that the β-trimethylsiloxy group can significantly suppress the direct 1,2-hydride shift from palladium carbene.
Oxidative aromatic C-O bond formation: synthesis of 3-functionalized benzo[b]furans by FeCl3-mediated ring closure of a-Aryl ketones
Liang, Zhidan,Hou, Weizhe,Du, Yunfei,Zhang, Yongliang,Pan, Yan,Mao, Deng,Zhao, Kang
supporting information; experimental part, p. 4978 - 4981 (2010/01/16)
A variety of 3-functionalized benzo[b]furans were achieved by way of a FeCl3-medlated Intramolecular cyclization of electron-rich a-aryl ketones. The alkoxy substituent on the benzene ring In the substrates was essential for an efficient cyclization to occur. This novel method allows the construction of benzo[b]furan rings by joining the O-atom on the side chain to the benzene ring via direct oxidative aromatic C-O bond formation.
Dynamic kinetic resolution in the asymmetrie synthesis of β-amino acids by organocatalytic reduction of enamines with trichlorosilane
Malkov, Andrei V.,Stoncius, Sigitas,Vrankova, Kvetoslava,Arndt, Matthias,Kocovsky, Pavel
supporting information; experimental part, p. 8082 - 8085 (2009/09/29)
A new methodology based on the organocatalytic asymmetric hydrosilylation of enamines that allows a direct access to a range of β3 and β2.3-amino acid derivatives was presented. The results show a successful reduction of aromatic substrates, a sterically more hindered ortho-substituted derivatives, and the thiophenyl analogue exhibiting lower reactivity. Fast enamine-imine equilibration is crucial as imines are chiral but racemic, while α-alkyl β-amino acids can be accessed by the symmetrical Mannich reaction. The α-alkyl derivatives have relative and absolute configuration due to their reduction with LiAlH4 into a known amino alcohols. Predominant formation of the anti isomer in 3o is consistent with conformation of the imine intermediate in the catalytic reduction.
CuI/L-proline-catalyzed coupling reactions of aryl halides with activated methylene compounds
Xie, Xiaoan,Cai, Guorong,Ma, Dawei
, p. 4693 - 4695 (2007/10/03)
(Chemical Equation Presented) The arylation of ethyl acetoacetate, ethyl benzoyl acetate, and diethyl malonate under the catalysis of Cul/L-proline in DMSO proceeds smoothly at 40-50°C in the presence of Cs2CO 3 to provide the 2-aryl
