60300-84-7Relevant academic research and scientific papers
A gold(i)-catalysed three-component reaction: Via trapping oxonium ylides with allenamides
Liu, Gengxin,Yu, Sifan,Hu, Wenhao,Qiu, Huang
, p. 12675 - 12678 (2019)
A gold(i)-catalysed three-component reaction between alcohols (and water), α-aryl-α-diazoesters and allenamides has been developed, affording three-component products, tert-allylic ethers (and alcohols), in moderate to excellent yields with excellent geom
Enantioselective Multicomponent Reaction for Rapid Construction of 1,2,5-Triol Derivatives with Vicinal Chiral Centers
Li, Mingfeng,Guo, Xin,Zheng, Qing,Hu, Wenhao,Liu, Shunying
, p. 5212 - 5221 (2017)
1,2,5-Triol derivatives with vicinal chiral centers have been synthesized from simple starting materials by one-pot method in good yields and with an excellent enantioselectivity. This process was promoted by a chiral secondary amine and iridium(I) cocata
Asymmetric Counter-Anion-Directed Aminomethylation: Synthesis of Chiral β-Amino Acids via Trapping of an Enol Intermediate
Kang, Zhenghui,Wang, Yongheng,Zhang, Dan,Wu, Ruibo,Xu, Xinfang,Hu, Wenhao
supporting information, p. 1473 - 1478 (2019/01/26)
A novel enantioselective aminomethylation reaction of diazo compound, alcohol and α-aminomethyl ether enabled by asymmetric counteranion-directed catalysis is disclosed that offers an efficient and convenient access to furnish optically active α-hydroxyl-β-amino acids in high yield with high to excellent enantioselectivities. Control experiments and DFT calculations indicate that the transformation proceeds through trapping the in situ generated enol intermediate with methylene iminium ion, and the asymmetric induction was enabled by chiral pentacarboxycyclopentadiene anion via H-bonding and electrostatic interaction.
Silica-supported HClO4 promotes catalytic solvent- and metal-free O-H insertion reactions with diazo compounds
Gallo, Rafael Douglas C.,Burtoloso, Antonio C. B.
, p. 4547 - 4556 (2018/10/17)
Solvent-free O-H insertion reactions in the presence of diazo carbonyl compounds were carried-out in very mild conditions. Unlike the traditional metal-catalysed version, employing rhodium acetate dimer, this method uses eco-friendly silica-supported HClO4 as the catalyst. Only 0.3 mol% of this Br?nsted acid catalyst, that can also be recycled several times, is necessary to guarantee very good yields (up to 97%) in the O-H insertion reactions. Reaction set-up is simple and permitted the preparation of forty-three α-hydroxy and α-alkoxy esters/ketones in just 1 h and at room temperature.
Facile synthesis of α-alkoxyl amides: Via scandium-catalyzed oxidative reaction between ynamides and alcohols
Zhang, Zhi-Xin,Zhu, Bo-Han,Xie, Pei-Xi,Tang, Jia-Qi,Li, Xin-Ling,Zhu, Chunyin,Yin, Ying-Wu,Ye, Long-Wu
, p. 18308 - 18315 (2018/05/30)
A novel and efficient scandium-catalyzed oxidative reaction between ynamides and alcohols for the facile synthesis of various α-alkoxyl amides is reported in this paper. The reaction avoids the need for the use of α-diazo carbonyls which are unstable and
Carbene Transfer and Carbene Insertion Reactions Catalyzed by a Mixed-Ligand Copper(I) Complex
Brenna, Stefano,Ardizzoia, G. Attilio
supporting information, p. 3336 - 3342 (2018/07/13)
The catalytic activity of the mixed-ligand copper(I) complex [Cu(PPh3)2(κ2-O,O"-lact)] (1) {lact = l-(+)-lactate} has been investigated in carbene transfer and carbene insertion reactions. Complex 1 catalytically promoted the diastereoselective cyclopropanation of olefins in the presence of ethyl diazoacetate (EDA), under mild conditions, and with a low catalyst loading (1 mol-%). In the case of internal alkenes, a trans/cis ratio of up to 93:7 was reached. Moreover, compound 1 easily promoted the insertion of the carbene fragment deriving from the decomposition of ethyl diazoacetate into O–H (alcohols and phenols) and N–H (amine) bonds, with formation of the corresponding ethyl 2-alkoxyacetate, ethyl 2-phenoxyacetate, and ethyl 2-aminoacetate derivatives in good to high yields.
Highly diastereoselective multicomponent cascade reactions: Efficient synthesis of functionalized 1-indanols
Jiang, Jun,Guan, Xiaoyu,Liu, Shunying,Ren, Baiyan,Ma, Xiaochu,Guo, Xin,Lv, Fengping,Wu, Xiang,Hu, Wenhao
supporting information, p. 1539 - 1542 (2013/04/23)
Trapped: A Michael-aldol-type cascade reaction including the trapping of an oxonium ylide through a delayed proton shift leads to the formation of multiple stereocenters in a mild one-pot synthesis. Enantiomerically pure indanol derivatives with four ster
Gold (I) catalysis of X-H bond insertions
Mangion, Ian K.,Weisel, Mark
experimental part, p. 5490 - 5492 (2010/10/20)
The utility of gold catalysis for carbene X-H bond insertion chemistry is described for the first time, taking advantage of the unique reactivity of sulfoxonium ylides as metal carbene precursors.
Rh(II) Catalyzed three-component reactions of diazoacetates with benzenemethanol and indane-1, 2, 3-triones
Guo, Xin,Wang, Jingjing,Yang, Liping,Hu, Wenhao
experimental part, p. 106 - 109 (2010/08/06)
A facile synthesis of 2-substituted-2-hydroxyindane-1,3-diones is reported via the reaction of diazoacetates with benzenemethanol and indane-1,2,3-triones catalyzed by dirhodium acetate.
Selectivity control in enantioselective four-component reactions of aryl diazoacetates with alcohols, aldehydes and amines: An efficient approach to synthesizing chiral β-amino-α-hydroxyesters
Xu, Xinfang,Zhou, Jing,Yang, Liping,Hu, Wenhao
scheme or table, p. 6564 - 6566 (2009/04/20)
Enantioselective four-component reactions of aryl diazoacetates with alcohols, aldehydes and amines catalyzed cooperatively by a rhodium complex and a chiral Bronsted acid produce β-amino-α-hydroxyl acid derivatives in a single step with excellent control
