2108-53-4Relevant academic research and scientific papers
Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?
Lang, Qiwei,Yang, Huaxin,Gu, Guoxian,Feng, Qiang,Wen, Jialin,Zhang, Xumu
, p. 933 - 936 (2021/03/03)
The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.
Synthesis of 2,3,4-Trisubstituted 2-Cyclopentenones via Sequential Functionalization of 2-Cyclopentenone
Chaudhari, Pankaj,Ghorai, Sujit K.,Gowala, Tarak N.,Pabba, Jagadish,Pal, Sitaram,Sawant, Krishna
, p. 10812 - 10818 (2021/07/31)
The synthesis of differently substituted 2,3,4-triarylcyclopent-2-en-1-ones from 2-cyclopentenone via sequential functionalization of a novel 2,4-dibromo-3-(4-methoxyphenyl) cyclopent-2-en-1-one intermediate has been developed. The process provides access
Nickel-catalyzed cross-coupling of β-carbonyl alkenyl pivalates with arylzinc chlorides
Pan, Wen-Jing,Wang, Zhong-Xia
, p. 1029 - 1036 (2018/02/19)
The nickel-catalyzed cross-coupling reaction of β-carbonyl alkenyl pivalates with arylzinc reagents generates 3-aryl-substituted α,β-unsaturated carbonyl compounds via C-O bond cleavage. The reaction features mild reaction conditions, a wide scope of substrates, and good functional group tolerance.
Selective Heck reaction of electron-rich aryl bromides with cyclic alkenones
Gowala, Tarak Nath,Pabba, Jagadish
supporting information, p. 1801 - 1804 (2015/03/30)
A simple and efficient protocol for the Heck reaction of cyclic alkenones with electron-rich aryl bromides has been developed. A ligand combination of X-Phos and tri-tert-butylphosphonium hydrogen tetrafluoroborate in the presence of Pd(PPh3)s
Isopropylmagnesium chloride-promoted unilateral addition of Grignard reagents to β-diketones: One-pot syntheses of β-tertiary hydroxyl ketones or 3-substituted cyclic-2-enones
Yuan, Rui,Zhao, Dan,Zhang, Li-Yuan,Pan, Xiang,Yang, Yan,Wang, Pei,Li, Hong-Feng,Da, Chao-Shan
supporting information, p. 724 - 728 (2016/01/12)
The regioselective unilateral additions of Grignard reagents to acyclic or cyclic β-diketones were effectively promoted by sub-stoichiometric amounts of i-PrMgCl to afford β-tertiary hydroxyl ketones or 3-substituted cyclic-2-enones, respectively. Also, the addition of Grignard reagents to acyclic β-diketones followed by a reaction with cyclic β-diketones in a one-pot process was put forward. The reaction mechanism was discussed in detail to explain the high regioselectivity via chemical experiments, hydrogen-deuterium exchange and mass spectrometry.
Asymmetric [5+3] formal cycloadditions with cyclic enones through cascade dienamine-dienamine catalysis
Yin, Xiang,Zheng, Yi,Feng, Xin,Jiang, Kun,Wei, Xue-Zhen,Gao, Ning,Chen, Ying-Chun
supporting information, p. 6245 - 6248 (2014/06/23)
A few aminocatalytic modes, such as iminium ions and different dienamines, have provided versatile tools for the functionalization of cyclic enones at various sites. Described here is a previously unreported cascade dienamine/dienamine catalytic pathway for β-substituted 2-cyclopentenones, and even 2-cyclohexenone. It involves domino α′-regioselective Michael addition and a γ-regioselective Mannich reaction with 3-vinyl-1,2-benzoisothiazole-1,1-dioxides to give fused or bridged architectures, which incorporate a spirocyclic skeleton, in excellent stereocontrol, thus furnishing unusual [5+3] formal cycloaddition reactions. Moreover, preliminary biological assays showed that some of the chiral products exhibited promising activity against some cancer cell lines, thus indicating that such skeletons might serve as leads in drug discovery.
Ligand- and base-free Pd(II)-catalyzed controlled switching between oxidative heck and conjugate addition reactions
Walker, Sarah E.,Boehnke, Julian,Glen, Pauline E.,Levey, Steven,Patrick, Lisa,Jordan-Hore, James A.,Lee, Ai-Lan
supporting information, p. 1886 - 1889 (2013/06/04)
A simple change of solvent allows controlled and efficient switching between oxidative Heck and conjugate addition reactions on cyclic Michael acceptor substrates, catalyzed by a cationic Pd(II) catalyst system. Both reactions are ligand- and base-free and tolerant of air and moisture, and the controlled switching sheds light on some of the factors which favor one reaction over the other.
Selective arylation at the vinylic site of cyclic olefins
Wu, Xiaojin,Zhou, Jianrong
supporting information, p. 4794 - 4796 (2013/06/05)
Cyclic olefins usually give Heck products having an aryl ring residing at the allylic or homoallylic position. We describe herein a new method that allows arylation at the vinylic position of various cyclic olefins.
CYCLIC AMINE SUBSTITUTED OXAZOLIDINONE CETP INHIBITOR
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Page/Page column 101, (2012/05/19)
CCompounds having the structure of Formula I, including pharmaceutically acceptable salts of the compounds, are CETP inhibitors and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In the compound of Formula I, A3 is a substitiuted phenyl group or indanyl group.Formula (I)
Ruthenium-catalyzed cyclization of 2-alkyl-1-ethynylbenzenes via a 1,5-hydrogen shift of ruthenium-vinylidene intermediates
Odedra, Arjan,Datta, Swarup,Liu, Rai-Shung
, p. 3289 - 3292 (2008/02/03)
(Chemical Equation Presented) Catalytic cyclization of 2-alkyl-1- ethynylbenzene derivatives was implemented by TpRuPPh3(CH 3CN)2PF6 (10 mol %) in hot toluene (105 °C, 36-100 h) to form 1-substituted-1H-indene and 1-indanone products; such cyclizations proceeded more efficiently for substrates bearing electron-rich benzenes. We propose that the cyclization mechanism involves a 1,5-hydrogen shift of initial metal-vinylidene intermediate.
