20859-19-2Relevant academic research and scientific papers
Palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones for the synthesis oftranscycloalkanols through dynamic kinetic resolution under acidic conditions
Li, Xiang,Zhao, Zi-Biao,Chen, Mu-Wang,Wu, Bo,Wang, Han,Yu, Chang-Bin,Zhou, Yong-Gui
supporting information, p. 5815 - 5818 (2020/06/03)
The first efficient palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones has been described through dynamic kinetic resolution under acidic conditions, providing a facile access to chiraltranscycloalkanol derivatives with excellent enantioselectivities.
Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Br?nsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions
Gheewala, Chirag D.,Hirschi, Jennifer S.,Lee, Wai-Hang,Paley, Daniel W.,Vetticatt, Mathew J.,Lambert, Tristan H.
supporting information, p. 3523 - 3527 (2018/03/21)
An enantioselective catalytic inverse-electron-demand Diels-Alder reaction of salicylaldehyde acetal-derived oxocarbenium ions and vinyl ethers to generate 2,4-dioxychromanes is described. Chiral pentacarboxycyclopentadiene (PCCP) acids are found to be effective for a variety of substrates. Computational and X-ray crystallographic analyses support the unique hypothesis that an anion with point-chirality-induced helical chirality dictates the absolute sense of stereochemistry in this reaction.
α-iodocycloalkenones: Synthesis of (±)-epibatidine
Sirisoma, Nilantha S.,Johnson, Carl R.
, p. 2059 - 2062 (2007/10/03)
A synthesis of the non-opiate analgesic alkaloid epibatidine was achieved in 13 steps and 13% Overall yield starting from 1,3-cyclohexadiene using in a key step a modified Stille coupling reaction on an α- iodocyclohexenone.
The stereochemistry of hippurate alkylation
McIntosh, John M.,Kiser, E. Jay,Tian, Zhigang
, p. 147 - 151 (2007/10/03)
Alkylation of the hippurate esters of trans 2-(p-substituted phenyl)cyclohexanol with benzyl bromide affords phenylalanine derivatives in high chemical yield. The reaction stereoselectivity varies from 20 to >98% depending on the aromatic group in the cyclohexyl auxiliary. A model that correctly predicts the sense of the induction is proposed.
Asymmetric synthesis of CDP840 by Jacobsen epoxidation. An unusual syn selective reduction of an epoxide
Lynch,Choi,Churchill,Volante,Reamer,Ball
, p. 9223 - 9228 (2007/10/03)
An asymmetric synthesis of the PDE IV inhibitor, CDP840 (3) is reported. The absolute stereochemistry was controlled by a Jacobsen epoxidation of the Z triaryl olefin 8 (89% ee) or the E triaryl olefin 9 (48% ee). The disparate results in stereocontrol were interpreted in terms of the 'skewed side-on approach model' proposed by Jacobsen. LiBH4 · BH3 reduction of the epoxides was found to proceed with retention of configuration.
Inhibitors of acyl CoA:cholesterol acyltransferase
Vaccaro, Wayne,Amore, Cindy,Berger, Joel,Burrier, Robert,Clader, John,Davis, Harry,Domalski, Martin,Fevig, Tom,Salisbury, Brian,Sher, Rosy
, p. 1704 - 1719 (2007/10/03)
Conformational restriction of previously disclosed acyclic diphenylethyl)diphenylacetamides led to the discovery of several potent inhibitors of acyl CoA:cholesterol acyltransferase (ACAT). cis-[2-(4- Hydroxyphenyl)-1-indanyl]diphenylacetamide (4a) was the most potent ACAT inhibitor identified (IC50 = 0.04 μM in an in vitro rat hepatic microsomal ACAT assay, ED50 = 0.72 mg/kg/day in cholesterol-fed hamsters).
Enzymatic resolution of trans-2-arylcyclohexan-1-ols using crude chicken liver esterase (CCLE) as biocatalyst
Basavaiah,Rao
, p. 223 - 234 (2007/10/02)
Homochiral trans-2-arylcyclohexan-1-ols were synthesized via crude chicken liver esterase (CCLE) mediated enantioselective hydrolysis of the corresponding racemic acetates.
Enantioselective synthesis using crude enzymes
Basavaiah, Deevi,Krishna, Peddinti Rama
, p. 131 - 134 (2007/10/02)
Chiral trans-2-aryloxycyclohexan-1-ols, trans-2-alkoxycyclohexan-1-ols, trans-2-arylcyclohexan-1-ols, homoallyl alcohols, 1-aryl-1-alkanols, 1,2-diphenylethane-1,2-diol are prepared in high optical purities via enantioselective hydrolysis of acetates of the corresponding racemic alcohols using crude enzymes such as pig liver acetone powder (PLAP), goat liver acetone powder (GLAP), chicken liver acetone powder (CLAP) and bovine liver acetone powder (BLAP).
BORON FLUORIDE PROMOTED OPENING OF EPOXIDES BY ORGANOCOPPER AND CUPRATE REAGENTS
Alexakis, A.,Jachiet, D.,Normant, J. F.
, p. 5607 - 5620 (2007/10/02)
In the presence of BF3 the reaction rate of organocopper and cuprate reagents with poorly reactive epoxides is dramatically enhanced.Lithium organocuprates are the best choice among the various organocopper and cuprate reagents tested.Even the dimesityl cyanocuprate is able to react with cyclohexene oxide in excellent yield.No products of cationic rearrangements are observed.The reaction with various epoxides shows a complete stereochemical (pure anti opening) and regiochemical control (attack on the less hindered side of the epoxide).
The Stability of Allylic and Vinylic Deuterium Atoms During the Lithium/Ammonia Reduction of Some Styrenoid Systems
Collins, David J.,Molinski, Tadeusz F.,Sjoevall, Jan
, p. 361 - 370 (2007/10/02)
Reduction of 2-(p-methoxyphenyl)cyclohexan-1-one (8) with lithium aluminium deuteride followed by acetylation gave trans-1-acetoxy-2-(p-methoxyphenyl)(1-2H1)cyclohexane (10b).Base-catalysed deuteration of 2-(p-methoxyphenyl)cyclohexan-1-one (8) afforded t
