39568-04-2Relevant academic research and scientific papers
"on water" palladium catalyzed diastereoselective boronic acid addition to structurally diverse cyclopropane nitriles
Das, Asish R.,Das, Dwaipayan,Mukherjee, Prasun
, p. 8886 - 8898 (2020/11/23)
An efficient palladium catalyzed diastereoselective addition of arylboronic acids to complex spirocyclopropyl dinitriles is developed in the presence of a catalytic amount of 4-dodecylbenzenesulphonic acid (DBSA) as a Br?nsted acid surfactant in aqueous media. The protocol is also found to be highly effective when different types of nitrile compounds and organo-boron compounds are used. The overall reaction has been found to be very cost efficient since it requires low catalyst loading, mild thermal energy and short reaction time. Wide substrate scope, operational simplicity, good to excellent product yield, and use of green solvents make the reaction a practical route to transform nitrile into a keto functionality in biorelevant heterocyclic scaffolds. The scale-up synthesis of the target scaffolds can also be achieved with ease which also signifies the practicability of this protocol. This journal is
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.).
Recycling Catalyst as Reactant: A Sustainable Strategy to Improve Atom Efficiency of Organocatalytic Tandem Reactions
Wei, Wen,Tang, Yuhai,Zhou, Yan,Deng, Ge,Liu, Ziyu,Wu, Jun,Li, Yang,Zhang, Junjie,Xu, Silong
supporting information, p. 6559 - 6563 (2018/10/20)
A sustainable strategy by internally recycling an organocatalyst as a reactant in a downstream reaction to improve the atom efficiency of organocatalytic tandem reactions is described. Specifically, a one-pot tandem Cloke-Wilson/Boulton-Katritzky reaction
Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans
Zhang, Jingfang,Tang, Yuhai,Wei, Wen,Wu, Yong,Li, Yang,Zhang, Junjie,Zheng, Yuansuo,Xu, Silong
supporting information, p. 3043 - 3046 (2017/06/23)
An organocatalytic Cloke-Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in gener
Asymmetric Ring Opening/Cyclization/Retro-Mannich Reaction of Cyclopropyl Ketones with Aryl 1,2-Diamines for the Synthesis of Benzimidazole Derivatives
Xia, Yong,Lin, Lili,Chang, Fenzhen,Liao, Yuting,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 12228 - 12232 (2016/10/13)
A highly efficient asymmetric ring-opening/cyclization/retro-Mannich reaction of cyclopropyl ketones with aryl 1,2-diamines has been realized using a chiral N,N′-dioxide/ScIIIcatalyst. Benzimidazoles containing chiral side chains were generated under mild reaction conditions in excellent outcomes (up to 99 % yield and 97 % ee). This method also provides efficient access to chiral benzimidazole-substituted amide and cycloheptene derivatives.
Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde
Fu, Xuan,Lin, Lili,Xia, Yong,Zhou, Pengfei,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 5914 - 5917 (2016/07/06)
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).
An efficient synthesis of cycloalkane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using (1-aryl-2-bromoethyl)-dimethylsulfonium bromides: Application to a one-pot synthesis of tetrahydroindol-4(5H)-one
Nambu, Hisanori,Fukumoto, Masahiro,Hirota, Wataru,Ono, Naoki,Yakura, Takayuki
supporting information, p. 4312 - 4315 (2015/06/22)
An efficient synthesis of cyclohexane- and cyclopentane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using sulfonium salts was achieved. The reaction of 1,3-cycloalkanediones with (1-aryl-2-bromoethyl)-dimethylsulfonium bromides and powdered K2CO3 in EtOAc provided the corresponding spirocyclopropanes in high yields. Furthermore, a one-pot synthesis of tetrahydroindol-4(5H)-one from 1,3-cyclohexanedione was achieved using the present protocol and a sequential ring-opening cyclization of spirocyclopropane with a primary amine.
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 (2015/11/11)
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.
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
supporting information, p. 227 - 230 (2015/02/05)
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.
α-BROMOCYCLOPROPYLLITHIUM COMPOUNDS IN REACTIONS WITH CARBOXYLIC ACID CHLORIDES AND ESTERS
Kulinkovich, O. G.,Tishchenko, I. G.,Sviridov, S. V.
, p. 1682 - 1686 (2007/10/02)
The composition of the products from the reaction of α-bromocyclopropyllithium compounds with carboxylic acid chlorides and esters is determined by the transformations of the cyclopropyllithium enolates formed as a result of rapid halogen-lithium exchange between the initial organolithium compounds and the intermediate α-bromocyclopropyl ketones.In the case of the aliphatic carboxylic acid derivatives the main competing process is deprotonation of the substrate by the α-bromocyclopropyllithium reagent.
