65564-87-6Relevant 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
supporting information, 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.
A unified approach to sesquiterpenes sharing trimethyl(p-tolyl) cyclopentanes: Formal total synthesis of (±)-laurokamurene B
Das, Mrinal K.,Dinda, Bidyut K.,Bisai, Vishnumaya
supporting information, p. 2039 - 2042 (2019/07/08)
A unified approach to the sesquiterpenoids sharing common trimethyl(p-tolyl) cyclopentane skeleton has been disclosed via a key Stork-Danheiser sequence on a cyclopentane based vinylogous ester with aryl Grignard reagent followed by α-methylation strategy
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.
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.
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
2-(1-benzotriazolyl)pyridine: A robust bidentate ligand for the palladium-catalyzed C-C (Suzuki, Heck, Fujiwara-Moritani, Sonogashira), C-N and C-S coupling reactions
Verma, Akhilesh K.,Jha, Rajeev R.,Chaudhary, Ritu,Tiwari, Rakesh K.,Danodia, Abhinandan K.
, p. 421 - 438 (2013/05/08)
A new class of bidentate ligand, 1-(pyridine-2-yl)-1H-benzo[d][1,2,3] triazole has been designed and employed for the palladium-catalyzed C-C (Suzuki, Heck, Fujiwara-Moritani, and Sonogashira), C-N and C-S coupling reactions. The ligand was found to be inexpensive, thermally stable, easy to synthesize from easily accessible starting materials on a multigram scale, show simplicity in use, and robustness in application, making this ligand effective for different coupling reactions. Suitably, the donor ability of the N=N bond of the benzotriazole ring and lone pair of electrons on the N of the pyridine ring enhance the bidentate ability of the ligand.
NOVEL ARYLBICYCLO[3.1.0]HEXYLAMINES AND METHODS AND COMPOSITIONS FOR THEIR PREPARATION AND USE
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Page/Page column 56-57, (2008/12/05)
The invention provides novel arylbicyclo[3.1.OJhexylamines, and related processes and intermediates for preparing these compounds, as well as compositions and methods employing these compounds for the treatment and/or prevention of central nervous system
Palladium-catalyzed intramolecular 5-endo-trig oxidative Heck cyclization: a facile pathway for the synthesis of some sesquiterpene precursors
Ray, Devalina,Paul, Sunanda,Brahma, Sulagna,Ray, Jayanta. K.
, p. 8005 - 8008 (2008/03/18)
An efficient and convenient method for the construction of substituted cyclopentenones via palladium-catalyzed intramolecular 5-endo-trig oxidative cyclization has been introduced as a powerful new strategy for the synthesis of sesquiterpenes.
Chemospecificity in arylations of δ- and γ-ketocarboxylic acids with P2O5-MsOH, TfOH, and related acidic media
Yonezawa, Noriyuki,Koike, Masayuki,Kameda, Asami,Naito, Shin,Hino, Tetsuo,Maeyama, Katsuya,Ikeda, Tomiki
, p. 3169 - 3180 (2007/10/03)
Remarkable contrast between chemospecificities in acid-mediated arylation of δ- and γ-ketocarboxylic acids was revealed: in the presence of P2O5-MsOH, TfOH, PPA, and MsOH, arylation of δ-ketocarboxylic acid 1A with arenes takes place
Two methods for the preparation of 2-cyclohexenones from resin-bound 1,3-cyclohexanedione
Fraley, Mark E.,Rubino, Robert S.
, p. 3365 - 3368 (2007/10/03)
The addition of organolithium or Grignard reagents to viny]ogous ester resin 1 followed by mild hydrolysis of product resins 2 provides 3-alkyl-2-cyclohexenones in high purity (>95%). Alternatively, conversion of 1 to vinyl triflate resin 4 followed by palladium-mediated couplings with aryl boronic acids and hydrolysis furnishes 3-ary]-2-cyclohexenones in lower yield, but exceptional purity.
