135095-89-5Relevant academic research and scientific papers
Homogeneous dihydroxylation of olefins catalyzed by a recyclable OsO42 - core dendrimer
Fujita, Ken-ichi,Ainoya, Taku,Tsuchimoto, Teruhisa,Yasuda, Hiroyuki
, p. 808 - 810 (2010)
By employing an osmate (OsO42 -) core dendrimer as a catalyst, homogeneous dihydroxylation reactions proceeded rapidly, and the dendritic osmium catalyst was efficiently recycled by reprecipitation.
Photo-Induced Dihydroxylation of Alkenes with Diacetyl, Oxygen, and Water
Masuda, Yusuke,Ikeshita, Daichi,Murakami, Masahiro
, (2021/02/09)
Herein reported is a photo-induced production of vicinal diols from alkenes under mild reaction conditions. The present dihydroxylation method using diacetyl (= butane-2,3-dione), oxygen, and water dispenses with toxic reagents and intractable waste generation.
Catalytic Asymmetric Acyloin Rearrangements of α-Ketols, α-Hydroxy Aldehydes, and α-Iminols by N, N′-Dioxide-Metal Complexes
Dai, Li,Li, Xiangqiang,Zeng, Zi,Dong, Shunxi,Zhou, Yuqiao,Liu, Xiaohua,Feng, Xiaoming
, p. 5041 - 5045 (2020/07/03)
A highly enantioselective acyloin rearrangement of cyclic α-ketols has been developed with a chiral Al(III)-N,N′-dioxide complex as catalyst. This strategy provided an array of optically active 2-acyl-2-hydroxy cyclohexanones in moderate to good yields with high enantioselectivities. The asymmetric isomerizations of acyclic α-hydroxy aldehydes and α-iminols were achieved as well under modified conditions, affording the corresponding chiral α-hydroxy ketones and α-amino ketones in moderate results. Moreover, further transformations of product to enantioenriched diols were carried out.
Direct Asymmetric α-Hydroxylation of Cyclic α-Branched Ketones through Enol Catalysis
Shevchenko, Grigory A.,Pupo, Gabriele,List, Benjamin
, p. 49 - 53 (2019/01/04)
Enantiopure α-hydroxy carbonyl compounds are common scaffolds in natural products and pharmaceuticals. Although indirect approaches towards their synthesis are known, direct asymmetric methodologies are scarce. Herein, we report the first direct asymmetric α-hydroxylation of α-branched ketones through enol catalysis, enabling a facile access to valuable α-keto tertiary alcohols. The transformation, characterized by the use of nitrosobenzene as the oxidant and a new chiral phosphoric acid as the catalyst, delivers a good scope and excellent enantioselectivities.
Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles
Zhu, Jie,Sun, Xiao-Tao,Wang, Xiao-Dong,Wu, Lei
, p. 1788 - 1792 (2018/04/30)
A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and high reaction efficiency and enantioselectivity were maintained.
Bronsted Acid Mediated Direct α-Hydroxylation of Cyclic α-Branched Ketones
Shevchenko, Grigory A.,Dehn, Stefanie,List, Benjamin
supporting information, p. 2298 - 2300 (2018/10/20)
We report a Bronsted acid mediated direct α-hydroxylation of cyclic α-branched ketones via a tandem aminoxylation/N-O bond-cleavage process. Nitrosobenzene is used as the oxidant and subsequently promotes the liberation of the free alcohol. The desired pr
Green Organocatalytic Dihydroxylation of Alkenes
Theodorou, Alexis,Triandafillidi, Ierasia,Kokotos, Christoforos G.
, p. 1502 - 1509 (2017/04/01)
An inexpensive, green, metal-free one-pot procedure for the dihydroxylation of alkenes is described. H2O2 and 2,2,2-trifluoroacetophenone were employed as the oxidant and organocatalyst, respectively, in this highly sustainable protocol in which a variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in good to excellent yields. This process takes advantage of an epoxidation reaction followed by an acidic treatment in which water participates in the ring opening of the in situ prepared epoxide to lead to the desired product.
Osmium on chelate resin: Nonvolatile catalyst for the synthesis of DIOLS from alkenes
Monguchi, Yasunari,Wakayama, Fumika,Takada, Hitoshi,Sawama, Yoshinari,Sajiki, Hironao
supporting information, p. 700 - 704 (2015/03/14)
Osmium tetraoxide (OsO4) was immobilized on a commercially available chelate resin DIAION CR11 (CR11) just by simply immersing it in a methanol solution of OsO4 at room temperature. The resulting purple solid, 5% Os/CR11, indicated no volatility, and effectively catalyzed the oxidation of various alkenes to the corresponding diols.
Novel biphenyl organocatalysts for iminium ion-catalyzed asymmetric epoxidation
Farah, Mohamed M.,Page, Philip C. Bulman,Buckley, Benjamin R.,Blacker, A. John,Elsegood, Mark R.J.
, p. 758 - 769 (2013/07/27)
Two novel chiral biphenyl iminium salts derived from L-acetonamine, containing electron-withdrawing 3,30-substituents on the biphenyl unit, have been prepared and tested as asymmetric catalysts for epoxidation of prochiral alkenes. The results are compared with those achieved using the corresponding unsubstituted system.
Enantioselective titanium(III)-catalyzed reductive cyclization of ketonitriles
Streuff, Jan,Feurer, Markus,Bichovski, Plamen,Frey, Georg,Gellrich, Urs
supporting information; experimental part, p. 8661 - 8664 (2012/09/21)
Reduction, please! The title reaction affords ?-hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa-titanocene 1 was found to be an efficient catalyst for this process, which presumably proceeds by addition of a ketyl radical to a nitrile.
