187401-48-5Relevant academic research and scientific papers
Generation of α-Boryl Radicals and Their Conjugate Addition to Enones: Transition-Metal-Free Alkylation of gem-Diborylalkanes
Wu, Chaoqiang,Bao, Zhicheng,Dou, Bowen,Wang, Jianbo
supporting information, p. 2294 - 2298 (2021/01/18)
A transition-metal-free method for the alkylation of gem-diborylalkanes with α,β-unsaturated ketones has been developed. It is demonstrated that the α-boryl radicals can be generated efficiently from gem-diborylalkanes with the aid of catechol and oxidants. The α-boryl radicals formed through such process can be engaged in conjugate addition reaction with α,β-unsaturated ketones. This transformation is a straightforward method for the synthesis of γ-borylketones.
Copper-Catalyzed Asymmetric Hydrosilylation of β-Nitroethyl Aryl Ketones
Zeng, Weijun,Tan, Xuefeng,Yu, Yang,Chen, Gen-Qiang,Zhang, Xumu
supporting information, p. 858 - 862 (2020/01/31)
A copper-catalyzed asymmetric hydrosilylation of β-nitroethyl aryl ketones has been disclosed, and the corresponding chiral alcohols could be obtained in high yields (up to 99% yield) and excellent enantioselectivities (up to 96% ee). Moreover, the reaction worked well on a gram scale with 0.3 mol % of ligand loading, indicating that our protocol has potential applications in the synthesis of important pharmaceuticals such as Tranylcypromine and Ticagrelor.
Photocatalytic C(sp3)?H Activation towards α-methylenation of Ketones using MeOH as 1 C Source Steering Reagent
Verma, Fooleswar,Shukla, Prashant,Bhardiya, Smita R.,Singh, Manorama,Rai, Ankita,Rai, Vijai K.
supporting information, (2019/02/05)
Unprecedented direct access to terminal enones via α-methylenation of aryl ketones to form C=C bond is achieved under visible-light conditions using methanol as one carbon source substrate and solvent as well. The reaction involves Cu@g-C3N4-catalysed in situ oxidation of methanol into formaldehyde followed by dehydrative cross aldol type reaction. Various aryl ketones react efficiently with MeOH, producing α,β-unsaturated carbonyl compounds only in 4–8 h at room temperature in excellent yield (84–97%). Operational simplicity, wide substrate scope, ambient reaction conditions, visible-light photocatalysis and novel application of MeOH as methylene donor substrate are the salient features making the envisaged protocol mild, efficient and green alternative to the existing methods for synthesis of such fine chemicals. (Figure presented.).
Manganese-Catalyzed Ring-Opening Coupling Reactions of Cyclopropanols with Enones
Zhang, Yong-Hui,Zhang, Wen-Wei,Zhang, Ze-Yu,Zhao, Kai,Loh, Teck-Peng
, p. 5101 - 5105 (2019/07/03)
A manganese-catalyzed ring-opening coupling reaction of cyclopropanols with enones for the facile and efficient preparation of 1,6-diketones is described. A wide array of synthetically important 1,6-diketones bearing manifold functional groups are obtained with up to 93% yield. These reactions feature broad substrate scopes, environmentally benign conditions, inexpensive catalyst, and operational simplicity.
Photochemical Alkene Isomerization for the Synthesis of Polysubstituted Furans and Pyrroles under Neutral Conditions
Walker, Johannes C. L.,Werrel, Simon,Donohoe, Timothy J.
, p. 13114 - 13118 (2019/10/22)
A photochemical approach to polysubstituted heterocycles using UV-induced alkene isomerization is described. The method allows for the synthesis of disubstituted furans and pyrroles under mild and neutral conditions and also provides access to a class of trisubstituted furans pertinent to natural-product synthesis. The method has broad functional-group tolerance and many richly decorated heterocycles have been prepared incorporating functional groups that are unstable under Br?nsted and Lewis acidic conditions.
Indium(III)-Catalyzed Hydration and Hydroalkoxylation of α,β-Unsaturated Ketones in Aqueous Media
Yun, Jin-Jin,Zhi, Man-Ling,Shi, Wen-Xiao,Chu, Xue-Qiang,Shen, Zhi-Liang,Loh, Teck-Peng
supporting information, p. 2632 - 2637 (2018/05/30)
The hydration of α,β-unsaturated ketones with water proceeded efficiently in the presence of In(OTf)3 (20 mol%) in aqueous media to afford synthetically versatile β-hydroxyketones in moderate to good yields with good functional group compatibility. The method also can be extended to the hydroalkoxylation of α,β-unsaturated ketones with various alcohols for the efficient synthesis of β-alkoxyketones as well as tetrahydrofuran derivatives. (Figure presented.).
Chromium(III)-Catalyzed Addition of Water and Alcohol to α,β-Unsaturated Ketones for the Synthesis of β-Hydroxyl and β-Alkoxyl Ketones in Aqueous Media
Yun, Jin-Jin,Liu, Xuan-Yu,Deng, Wei,Chu, Xue-Qiang,Shen, Zhi-Liang,Loh, Teck-Peng
, p. 10898 - 10907 (2018/09/06)
An efficient chromium(III) chloride-catalyzed Michael-type reaction of water or alcohol with α,β-unsaturated ketones is developed. A variety of α,β-unsaturated ketones effectively reacted with either water or alcohols to give the corresponding β-hydroxyl ketones or β-alkoxyl ketones in modest to high yields with excellent compatibility to various functional groups. The approach was further utilized for the preparation of synthetically useful compounds containing tetrahydrofuran skeleton.
Transition Metal-Free α-Csp3-H Methylenation of Ketones to Form C=C Bond Using Dimethyl Sulfoxide as Carbon Source
Liu, Yu-Feng,Ji, Peng-Yi,Xu, Jing-Wen,Hu, Yu-Qun,Liu, Qiang,Luo, Wei-Ping,Guo, Can-Cheng
, p. 7159 - 7164 (2017/07/26)
A direct α-Csp3-H methylenation of arylketones to form C=C bond using dimethyl sulfoxide as one-carbon source is achieved under transition metal-free reaction condition. Various aryl ketone derivatives react readily with DMSO, producing the α,β-unsaturated carbonyl compounds in yields of 42 to 90%. This method features a transition metal-free reaction condition, wide substrate scope and using DMSO as novel one-carbon source to form C=C bond, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyl compounds. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.
Iron-catalyzed α-methylenation of ketones with N,N-Dimethylacetamide: An approach for α,β-unsaturated carbonyl compounds
Li, Yi-Ming,Lou, Shao-Jie,Zhou, Qin-Hua,Zhu, Lian-Wen,Zhu, Long-Feng,Li, Lei
supporting information, p. 3044 - 3047 (2015/05/13)
In this study, we developed a general iron-catalyzed α-methylenation of ketones by using N,N-dimethylacetamide as the one-carbon source. Various ketones, including aryl and alkyl ketones, enones, and dicarbonyl compounds were well tolerated to yield the corresponding α,β-unsaturated carbonyl compounds in the presence of an iron catalyst, peroxides, and N,N-dimethylacetamide under aerobic conditions. A general and facile iron-catalyzed α-methylenation of carbonyl compounds by using N-methyl amides as the one-carbon source was developed. Various carbonyl compounds (aryl- or alkyl-substituted, enones, 1,3-dicarbonyl compounds) were well tolerated to furnish the corresponding α,β-unsaturated carbonyl compounds in the presence of an iron catalyst, peroxides, and N-methyl amides under aerobic conditions.
Carboxylic acid derivatives having fused rings
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, (2008/06/13)
The present invention provides a medicament exhibiting excellent retinoic acid receptor agonism. A Carboxylic acid derivative having a fused ring which is represented by the following formula or a pharmacologically acceptable salt thereof: {wherein the symbol represents a single bond or a double bond; X, Y, Z, P, Q, U, V and W are each a group represented by the formula: -O- or -S-, or a group represented by the formula: [wherein Rk (k: 1 to 8) is hydrogen, halogeno, optionally substituted lower alkyl or the like, with either of R7 and R8 being a group represented by the formula: (wherein A and B are each independently an optionally substituted aromatic hydrocarbon ring or an optionally substituted unsaturated heterocycle; and D is optionally protected carboxyl)]}.
