19775-91-8Relevant academic research and scientific papers
Asymmetric transfer hydrogenation of cycloalkyl vinyl ketones to allylic alcohols catalyzed by ruthenium amido complexes
Liu, Sensheng,Cui, Peng,Wang, Juan,Zhou, Haifeng,Liu, Qixing,Lv, Jinliang
, p. 264 - 267 (2019/01/10)
A chemoselective 1,2-reduction of cycloalkyl vinyl ketones via asymmetric transfer hydrogenation is described. The reduction proceeded smoothly with a chiral diamine ruthenium complex as a catalyst and a HCOOH-NEt3 azeotrope as both a hydrogen source and solvent under mild conditions. A wide range of 1-cycloalkyl chiral allylic alcohols were obtained in good yields and up to 87% ee. It was found that the alkyl group plays an important role in the enantioselectivity.
Br?nsted Acid Enabled Nickel-Catalyzed Hydroalkenylation of Aldehydes with Styrene and its Derivatives
Han, Xing-Wang,Zhang, Tao,Zheng, Yan-Long,Yao, Wei-Wei,Li, Jiang-Fei,Pu, You-Ge,Ye, Mengchun,Zhou, Qi-Lin
supporting information, p. 5068 - 5071 (2018/03/27)
A Br?nsted acid enabled nickel-catalyzed hydroalkenylation of aldehydes and styrene derivatives has been developed. The Br?nsted acid acts as a proton shuttle to transfer a proton from the alkene to the aldehyde, thereby leading to an economical and byproduct-free coupling. A series of synthetically useful allylic alcohols were obtained through one-step reactions from readily available styrene derivatives and aliphatic aldehydes in up to 88 % yield and with high linear selectivity.
Structure-based optimization of click-based histone deacetylase inhibitors
Hou, Jingli,Feng, Congran,Li, Zhonghua,Fang, Qinghong,Wang, Huihui,Gu, Guoxian,Shi, Yikang,Liu, Pi,Xu, Feng,Yin, Zheng,Shen, Jie,Wang, Peng
supporting information; experimental part, p. 3190 - 3200 (2011/07/29)
Previously, we reported a click-chemistry based approach to the synthesis of a novel class of histone deacetylase (HDAC) inhibitors [1]. The lead compound NSC746457 was found to be as potent as SAHA (Vorinostat). Further optimization of NSC746457 by using
Chemoselective conjugate reduction of α,β-unsaturated ketones catalyzed by rhodium amido complexes in aqueous media
Li, Xuefeng,Li, Liangchun,Tang, Yuanfu,Zhong, Ling,Cun, Linfeng,Zhu, Jin,Liao, Jian,Deng, Jingen
supporting information; experimental part, p. 2981 - 2988 (2010/07/05)
Although a notable feature of Noyori's Ru-TsDPEN complex is that the transfer hydrogenation reaction is highly chemoselective for the C-O functional group and tolerant of alkenes, our early report indicated that the chemoselectivity could be switched from C-O to C-C bonds in the transfer hydrogenation of activated α,β-unsaturated ketones. Now we have found that a variety of α,β-unsaturated ketones, even without other electron-withdrawing functional groups, could be reduced on the alkenic double bonds with high selectivities employing amido-rhodium hydride complex in aqueous media, and up to 100% chemoselectivity has been achieved. It is notable that the chemoselectivity was improved significantly on going from organic solvent to water. Moreover, a 1,4-addition mechanism has been proposed on the basis of the corresponding experimental details and computational analysis.
Nickel(0)-catalyzed formation of oxaaluminacyclopentenes via an oxanickelacyclopentene key intermediate: Me2AlOTf-assisted oxidative cyclization of an aldehyde and an alkyne with nickel(0)
Ohashi, Masato,Saijo, Hiroki,Arai, Tomoya,Ogoshi, Sensuke
scheme or table, p. 6534 - 6540 (2011/02/17)
The use of Me2AlOTf as an additive allowed the oxidative cyclization of pivalaldehyde and diphenylacetylene with nickel(0) in the presence of PCy3 to give an oxanickelacyclopentene, the structure of which was unambiguously determined
Remarkable Dependence of Diastereoselectivity on Anhydrous or Aqueous Solvent in the Indium Hydride Promoted Reductive Aldol Reaction of α,β-Unsaturated Ketones
Inoue, Katsuyuki,Ishida, Tatsuya,Shibata, Ikuya,Baba, Akio
, p. 283 - 287 (2007/10/03)
Dichloroindium hydride generated by the transmetallation between tributyltin hydride and indium trichloride predominantly reduced α,β-unsaturated ketones (enones) with 1,4-selectively even in the presence of aldehydes. Under anhydrous conditions, the successive aldol reaction between the resulting enolates and the remaining aldehydes proceeded with high anti-selectivity. The stereo-chemistry was dramatically reversed to be syn-selective by the use of water and methanol as an additive and solvent, respectively.
Effect of InCl3 on the addition of Grignard reagents to α,β-unsaturated carbonyl compounds
Kelly, Brian G.,Gilheany, Declan G.
, p. 887 - 890 (2007/10/03)
Control of 1,2- versus 1,4-addition of organometallic reagents to enones remains a long-standing problem. There is still no satisfactory 1,2-directing agent comparable to the 1,4-directing effect of copper salts. We report that the presence of just 5 mol% indium(III) chloride can significantly alter the amount of 1,2-product formed in these reactions.
Kinetic resolution of acyclic secondary allylic silyl ethers catalyzed by chiral ketones
Yang,Jiao,Yip,Lai,Wong
, p. 4619 - 4624 (2007/10/03)
Kinetic resolution of acyclic secondary allylic silyl ethers by chiral dioxiranes generated in situ from chiral ketones (R)-1 and (R)-2 and Oxone was investigated. An efficient and catalytic method has been developed for kinetic resolution of those substrates with a CCl3, tert-butyl, or CF3 group at the α-position. In particular, high selectivities (S up to 100) were observed for kinetic resolutions of racemic α-trichloromethyl allylic silyl ethers 7 and 9-15 catalyzed by ketones (R)-2. Both the recovered substrates and the resulting epoxides were obtained in high enantiomeric excess. On the basis of steric and electrostatic interactions between the chiral dioxiranes and the racemic substrates, a model was proposed to rationalize the enantioselectivities and diastereoselectivities in the chiral ketone-catalyzed kinetic resolution process.
