74431-38-2Relevant academic research and scientific papers
Resolution of C2-symmetric 9,10-dihydro-9,10-ethanoanthracene- 11,12- dicarboxylic acid and 2,3-diphenylsuccinic acid using (S)-proline
Ramanathan, C. Ramaraj,Periasamy, Mariappan
, p. 2651 - 2656 (1998)
Racemic 9,10-dihydro-9, 10-ethanoanthracene- 11,12-dicarboxylic acid is resolved to obtain the corresponding (S,S)-isomer in 96±2%, cc and the (R,R)-isomer in 97 ± 2% ee through complexation with (S)-proline in methanol. The racemic 2,3-diphenylsuccinic acid has been resolved to obtain the (S,S)-isomer in 93% ee using (S)-proline in methanol.
Dynamic kinetic resolution of bis-aryl succinic anhydrides: Enantioselective synthesis of densely functionalised γ-butyrolactones
Claveau, Romain,Twamley, Brendan,Connon, Stephen J.
, p. 3231 - 3234 (2018/04/05)
The efficient Dynamic Kinetic Resolution (DKR) of disubstituted anhydrides has been shown to be possible for the first time. Using an ad hoc designed organocatalyst and an enantio- and diastereoselective cycloaddition process with aldehydes, stereochemically complex γ-butyrolactone derivatives can be obtained-with control over three contiguous stereocentres, one of which is all carbon quaternary.
Efficient electrochemical dicarboxylation of phenyl-substituted alkenes: Synthesis of 1-phenylalkane-1,2-dicarboxylic acids
Senboku,Komatsu,Fujimura,Tokuda
, p. 418 - 420 (2007/10/03)
Electrochemical dicarboxylation of phenyl-substituted alkenes in the presence of atmospheric pressure of carbon dioxide with a platinum plate cathode and a magnesium rod anode readily took place efficiently in a DMF solution containing 0.1 M Et4NClO4 to give the corresponding 1,2-dicarboxylic acids in high yields.
Convenient synthetic methods to C2 symmetric 3,4-diphenylpyrrolidines
Rao, Vutukuri Dharma,Periasamy, Mariappan
, p. 703 - 706 (2007/10/03)
Convenient methods of synthesis of racemic and optically pure 3,4- diphenylpyrrolidine derivatives, involving oxidative coupling of ethyl phenylacetate using TiCl4/Et3N and reduction of the dl-2,3-diphenylsuccinic acid or the corresponding cyclic imide with NaBH4/I2 reagent in crucial steps, are described.
Asymmetric synthesis of optically active 2,3-diarylsuccinic acids by oxidative homocoupling of chiral 3-(arylacetyl)-2-oxazolidones
Kise, Naoki,Kumada, Kimikage,Terao, Yuichi,Ueda, Nasuo
, p. 2697 - 2708 (2007/10/03)
Oxidative homocoupling of chiral 3-(arylacetyl)-2-oxazolidones 1 was achieved by treatment with DABCO-TiCl4 or DMAP-TiCl4 and afforded the corresponding dimers stereospecifically. The reaction of (4S)- and (4R)-substituted 1 gave (S,S)- and (R,R)-dimers respectively. The obtained dimers were easily transformed to the corresponding 2,3-diaryl succinic acids. This reaction therefore provides a useful method For the synthesis of optically pure 2,3-diarylsuccinic acids. The oxidative coupling was not inhibited by para substitution of an electron donating group on the aryl group. A para-substituted electron withdrawing group and an ortho-substituent, however, hindered the coupling.
Dependence of the reactivities of titanium enolates on how they are generated: Diastereoselective coupling of phenylacetic acid esters using titanium tetrachloride
Matsumura, Yoshihiro,Nishimura, Maiko,Hiu, Hiroyuki,Watanabe, Mitsuaki,Kise, Naoki
, p. 2809 - 2812 (2007/10/03)
Oxidative coupling of phenylacetic acid esters was easily achieved by treating the esters with TiCl4 and then adding Et3N to the resulting solution. The products consisted of dl- and meso-2,3-diphenylsuccinic acid esters with the Claisen condensation product, and the ratio of these products depended on the reaction conditions. Reaction conditions suitable for high dl selectivity were determined, and a dimer of titanium enolate was postulated as an intermediate responsible for the high dl selectivity. The selectivities were compared with those in known oxidative couplings in which titanium enolate intermediates are prepared through lithium enolates and silyl enol ethers. The results suggest that the reactivities of titanium enolates intermediates depend on how they are generated.
Influence of β-arranged substituents in chiral seven-membered rhodium diphosphine rings on asymmetric hydrogenation of amino acid precursors
Krause, Hanswalter,Sailer, Cornelia
, p. 271 - 279 (2007/10/02)
Investigations concerning the optical induction in asymmetric hydrogenation reactions confirm the stereochemical control function of mono- and di-substituents in seven-membered chelate ring diphosphines, whereby the bulkiness of substituents in the backbone of the ligands is reflected in higher enantioselectivities.
NEW STEREOSELECTIVE METHOD FOR HYDROCARBON CHAIN CONSTRUCTION. CONVERSION OF N,N'-DIALKYL-N,N'-DIACYLHYDRAZINES TO DERIVATIVES OF THREO-1,2-DICARBOXYLIC ACIDS
Magedov, I.V.,Smushkevich, Yu. I.
, p. 632 - 636 (2007/10/02)
N,N'-Dialkyl-N,N'-diacylhydrazines are converted by the action of strong bases into N,N'-dialkylamides of threo-1,2-dicarboxylic acids.
Reaction of Dilithiated Carboxylic Acids with Iodine: Evidence for the Formation of a Radical Anion Intermediate
Renaud, Philippe,Fox, Marye Anne
, p. 3745 - 3752 (2007/10/02)
The mechanism for oxidative dimerization of carboxylic acid dianions involves single electron transfer to iodine, producing an organic anion radical.Rearrangement of this species was observed with suitable substrates at a rate competitive with intermolecular reactions.The radical anion can dimerize or react with iodine.The iodide thus generated can be isolated (reaction with excess of iodine) or can participate in a polar SN2-type reaction sequence leading to dimeric products (reaction with 1/2 equiv of iodine).The interference by free amines (liberated during the metalation with lithium amides) is rationalized by the formation of a charge-transfer complex with iodine which decomposes, liberating protons.
