1032818-10-2Relevant academic research and scientific papers
Diastereoselective Construction of Cyclopropane-Fused Tetrahydroquinolines via a Sequential [4 + 2]/[2 + 1] Annulation Reaction
Wang, Zhen-Hua,Shen, Li-Wen,Xie, Ke-Xin,You, Yong,Zhao, Jian-Qiang,Yuan, Wei-Cheng
, p. 3114 - 3118 (2020)
A sequential [4 + 2]/[2 + 1] annulation of α-aryl vinylsulfoniums with 2-aminochalcones and 2-(2-aminobenzylidene)-1H-indene-1,3(2H)-dione is reported that affords a series of cyclopropane-fused tetrahydroquinolines. The salient features of this novel and practical transformation include high efficiency, transition-metal-free nature, operational simplicity, and outstanding functional group tolerance.
Asymmetric synthesis of 2,3-dihydropyrroles by ring-opening/ cyclization of cyclopropyl ketones using primary amines
Xia, Yong,Liu, Xiaohua,Zheng, Haifeng,Lin, Lili,Feng, Xiaoming
, p. 227 - 230 (2015)
The asymmetric ring-opening/cyclization of cyclopropyl ketones with primary amine nucleophiles was catalyzed by a chiral N,N'-dioxide/scandium(III) complex through a kinetic resolution process. A broad range of cyclopropyl ketones and primary amines are suitable substrates of this reaction. The corresponding products were afforded in excellent enantioselectivities and yields (up to 97% ee and 98% yield) under mild reaction conditions. This method provides a promising access to chiral 2,3-dihydropyrroles as well as an effective procedure for the kinetic resolution of 2-substituted cyclopropyl ketones.
Asymmetric Ring-Opening of Cyclopropyl Ketones with Thiol, Alcohol, and Carboxylic Acid Nucleophiles Catalyzed by a Chiral N,N′-Dioxide-Scandium(III) Complex
Xia, Yong,Lin, Lili,Chang, Fenzhen,Fu, Xuan,Liu, Xiaohua,Feng, Xiaoming
, p. 13748 - 13752 (2015)
A highly efficient asymmetric ring-opening reaction of cyclopropyl ketones with a broad range of thiols, alcohols and carboxylic acids has been first realized by using a chiral N,N′-dioxide-scandium(III) complex as catalyst. The corresponding sulfides, ethers, and esters were obtained in up to 99 % yield and 95 % ee. This is also the first example of one catalytic system working for the ring-opening reaction of donor-acceptor cyclopropanes with three different nucleophiles, let alone in an asymmetric version.
Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde
Fu, Xuan,Lin, Lili,Xia, Yong,Zhou, Pengfei,Liu, Xiaohua,Feng, Xiaoming
, p. 5914 - 5917 (2016)
A highly diastereo- and enantioselective [3 + 3] annulation of donor-acceptor cyclopropanes with mercaptoacetaldehyde has been developed. In the presence of a N,N′-dioxide-Sc(iii) complex as the catalyst, a number of aromatic substituted cyclopropyl ketones reacted with mercaptoacetaldehyde smoothly, providing the corresponding chiral tetrahydrothiopyranols in moderate yields with excellent ee (up to 99% ee) and dr values (up to >19:1).
A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution
Lauder, Kate,Masci, Domiziana,Toscani, Anita,Al Mekdad, Aya,Black, Gary W.,Brown, Nicola L.,Turner, Nicholas J.,Luisi, Renzo,Castagnolo, Daniele
, p. 8982 - 8986 (2019)
A facile microwave assisted three-component protocol allows the synthesis of chiral aryl-1,2-mercaptoamines in water in a few minutes with high yields, bypassing the use of toxic aziridine intermediates. The chiral 1,2-mercaptoamines were then deracemized through enzymatic resolution of the racemates using monoamine oxidase (MAO-N) biocatalysts.
Diethylammonium iodide as catalyst for the metal-free synthesis of 5-aryl-2-oxazolidinones from aziridines and carbon dioxide
Bresciani, Giulio,Bortoluzzi, Marco,Pampaloni, Guido,Marchetti, Fabio
, p. 4152 - 4161 (2021/05/19)
The catalytic potential of ammonium halide salts was explored in the coupling reaction of a model aziridine with carbon dioxide, highlighting the superior activity of [NH2Et2]I. Then, working at room temperature, atmospheric CO2 pressure and in the absenc
Efficient Cycloaddition of CO2and Aziridines Activated by a Quadruple-Interpenetrated Indium-Organic Framework as a Recyclable Catalyst
Tian, Xue-Rui,Shi, Ying,Hou, Sheng-Li,Ma, Yue,Zhao, Bin
supporting information, p. 15383 - 15389 (2021/10/20)
On the basis of the global warming effect, it is of great significance to convert CO2 into the high value-added products oxazolidinones, but investigations on main-group-based metal-organic frameworks (MOFs) as heterogeneous catalysts still have not been
Iodine-Catalyzed Ring Opening of 1,1-Diacylcyclopropanes for Synthesis of Fully Substituted Pyrazole Derivatives
Bao, Yishu,Chen, Ming,Ding, Ziyu,Yang, Fulai,Yang, Xiuqin,Zhou, Qingfa,Zhu, Jin
supporting information, (2020/07/04)
An iodine-catalyzed [3+2] cycloaddition/ring opening reaction of 1,1-diacylcyclopropanes with sulfonyl hydrazides has been reported. In the presence of 20 mol-% iodine, a range of structurally diverse fully substituted pyrazoles with a hydroxy functional group are obtained in moderate to excellent yields with extremely high regioselectivity.
Two Stable Heterometal-MOFs as Highly Efficient and Recyclable Catalysts in the CO2 Coupling Reaction with Aziridines
Kang, Xiao-Min,Yao, Lin-Hong,Jiao, Zhuo-Hao,Zhao, Bin
supporting information, p. 3668 - 3674 (2019/08/01)
Two stable heterometal-organic frameworks, {Na[LnCo(DATP)2(Ac)(H2O)](NO3)?DMA?11 H2O}n (Ln=Er(1) and Yb(2)), have been prepared with H2DATP (4′-(3,5-dicarboxyphenyl)-2,2′:6′,2′′′-terpyridin
Chiral N,N′-Dioxide/ScΙΙΙ Complex-Catalyzed Asymmetric Ring-Opening Reaction of Cyclopropyl Ketones with Indoles
Chang, Fenzhen,Lin, Lili,Xia, Yong,Zhang, Hang,Dong, Shunxi,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 2608 - 2612 (2018/05/30)
The asymmetric ring-opening reaction of cyclopropyl ketones with indoles has been realized by using a N,N′-dioxide/scandium(ΙΙΙ) complex as catalyst. The corresponding 3-alkylated indole derivatives were obtained in moderate to excellent yields with good ee values. Moreover, a possible transition state was proposed on the basis of experimental studies and X-ray structure of product. (Figure presented.).
