88356-04-1Relevant academic research and scientific papers
Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones
Peters, Bram B. C.,Jongcharoenkamol, Jira,Krajangsri, Suppachai,Andersson, Pher G.
supporting information, p. 242 - 246 (2021/01/13)
Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.
Ruthenium-catalysed synthesis of chiral exocyclic allylic alcoholsviachemoselective transfer hydrogenation of 2-arylidene cycloalkanones
Zhang, Kaili,Liu, Qixing,He, Renke,Chen, Danyi,Deng, Zhangshuang,Huang, Nianyu,Zhou, Haifeng
supporting information, p. 1628 - 1632 (2021/03/09)
An exclusive asymmetric reduction of C=O bonds of 2-arylidene four-, five-, six-, and seven-membered cycloalkanones has been studied systematically. The asymmetric transfer hydrogenation was performed using a robust and commercially available chiral diamine-derived ruthenium complex as a catalyst and HCOOH/Et3N as a hydrogen source under mild conditions, giving 51 examples of chiral exocyclic allylic alcohols in up to 96% yield and 99% ee. This method was also applicable to the gram-scale synthesis of the active intermediates of the anti-inflammatory loxoprofen and natural product (?)-goniomitine.
A simple iron-catalyst for alkenylation of ketones using primary alcohols
Sk, Motahar,Kumar, Ashish,Das, Jagadish,Banerjee, Debasis
, (2020/04/10)
Herein, we developed a simple iron-catalyzed system for the α-alkenylation of ketones using primary alcohols. Such acceptor-less dehydrogenative coupling (ADC) of alcohols resulted in the synthesis of a series of important α,β-unsaturated functionalized ketones, having aryl, heteroaryl, alkyl, nitro, nitrile and trifluoro-methyl, as well as halogen moieties, with excellent yields and selectivity. Initial mechanistic studies, including deuterium labeling experiments, determination of rate and order of the reaction, and quantitative determination of H2 gas, were performed. The overall transformations produce water and dihydrogen as byproducts.
RuPHOX-Ru-Catalyzed Selective Asymmetric Hydrogenation of Exocyclic α,β-Unsaturated Pentanones
Li, Jing,Liu, Delong,Liu, Yangang,Lu, Yufei,Wang, Yanzhao,Zhang, Wanbin,Zhu, Yue
supporting information, (2019/08/26)
A RuPHOX-Ru catalyzed selective asymmetric hydrogenation of exocyclic α,β-unsaturated ketones has been developed, furnishing the corresponding chiral exocyclic allylic alcohols in high yields and with up to >99.5percent ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 10000 S/C) without any loss in reaction activity and enantioselectivity. The resulting hydrogenated products could be easily transformed to several biologically active compounds with high asymmetric performance. The asymmetric protocol provides an efficient methodology for the synthesis of chiral exocyclic allylic alcohols.
Fe3O4 nanoparticles as an efficient and magnetically recoverable catalyst for the synthesis of α β-unsaturated heterocyclic and cyclic ketones under solvent-free conditions
Alishiri, Tooba,Oskooei, Hossein A.,Heravi, Majid M.
, p. 3357 - 3362 (2013/10/01)
An efficient and green procedure has been developed for the synthesis of monoarylidenes of cyclic and heterocyclic ketones. The reaction was carried out under solvent-free conditions in the presence of a catalytic amount of nanosized magnetite (Fe3O4). The catalyst was easily removed by using an external magnet. The structures of the products were deduced from their 1H NMR, 13C NMR, and infrared spectroscopy and mass spectrometry. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Regioselective synthesis of dispirocycloalkanooxindolopyrrolidines and dispirocyclalkanoindanopyrrolidines
Poornachandran, Mahalingam,Jayagobi, Mathesan,Raghunathan, Raghavachary
body text, p. 551 - 563 (2010/04/06)
Synthesis of a series of novel dispirocycloalkanone-oxindolopyrrolidines and dispirocycloalkanone-indanopyrrolidines is described. The nonstabilized azomethine ylides generated from a secondary amino acid, sarcosine, and carbonyl components (isatin and ninhydrin) have been effectively trapped by the dipolarophiles, arylidene cycloalkanones, to afford dispiropyrrolidines. The one-pot azomethine ylide cycloaddition reactions were highly regioselective. Copyright Taylor & Francis Group, LLC.
Highly Enantioselective Hydrogenation of α-Arylmethylene Cycloalkanones Catalyzed by Iridium Complexes of Chiral Spiro Aminophosphine Ligands
Xie, Jian-Bo,Xie, Jian-Hua,Liu, Xiao-Yan,Kong, Wei-Ling,Li, Shen,Zhou, Qi-Lin
supporting information; experimental part, p. 4538 - 4539 (2010/06/17)
The highly efficient asymmetric hydrogenation of α-arylmethylene cycloalkanones catalyzed by Ir-complexes of chiral spiro aminophosphine ligands was developed, providing chiral exo-cyclic allylic alcohols at high yields with excellent enantioselectivities (up to 97% ee) and high turnover numbers (S/C up to 10,000). This new reaction provided an efficient method for the synthesis of the key intermediate of the active form of the anti-inflammatory loxoprofen.
Regioselective synthesis of rac-(1R,4R,6R,6aR)-6′-phenyl-7′, 8′-dihydro-1″H,2′H,6′H-dispiro[cycloalkane-1, 5′-pyrrolo[1,2-c][1,3]thiazole-4′,3″-indole]-2, 2″-diones through 3 + 2 cycloaddition reaction
Poornachandran, Mahalingam,Jayagobi, Mathesan,Raghunathan, Raghavachary
scheme or table, p. 240 - 243 (2009/12/07)
Synthesis of a series of novel rac-(1R,4R,6R,6aR)-6′-phenyl-7′, 8′-dihydro-1″H,2′H,6′H-dispiro[cycloalkane-1, 5′-pyrrolo[1,2-c][1,3]thiazole-4′,3″-indole]-2, 2″-diones by cycloaddition reaction is described. The nonstabilised azomethine ylide generated by the reaction of isatin and thiazolidine-2- carboxylic acid has been regioselectively trapped by various substituted benzylidene cycloalkanones.
Highly enantioselective synthesis of optically active ketones by iridium-catalyzed asymmetric hydrogenation
Lu, Sheng-Mei,Bolm, Carsten
supporting information; experimental part, p. 8920 - 8923 (2009/05/30)
(Chemical Equation Presented) Close to perfect enantioselectivity (up to 99% ee, see scheme) is found for the formation of α-substituted ketones by the asymmetric hydrogenation of enones with an iridium-phosphinooxazoline catalyst. In an operationally simple process, both linear and cyclic substrates react well and afford the desired products in high yields. A wide variety of substituents are tolerated, thus making the method synthetically appealing.
Lithium naphthalenide induced reductive selenenylation of α-cyano ketones: A regiocontrolled process for α-phenylseleno ketones and one-pot conversion into enone system
Zhu, Jia-Liang,Ko, Yen-Chun,Kuo, Chun-Wei,Shia, Kak-Shan
, p. 1274 - 1278 (2008/01/08)
An efficient procedure for the regiocontrolled synthesis of α-phenylseleno ketones has been developed, making use of the lithium naphthalenide induced reductive selenenylation of the α-cyano ketone system as a key operation. Moreover, seleno ketones thus generated in situ, upon subsequent treatment with hydrogen peroxide and acetic acid, could be further converted into the corresponding enones with a high degree of regioselectivity, presumably due to the lithium salt mediated selenoxide syn-elimination process. Georg Thieme Verlag Stuttgart.
