19144-86-6Relevant articles and documents
Solvent-induced chirality control in the enantioseparation of 1-phenylethylamine via diastereomeric salt formation
Kodama, Koichi,Kimura, Yuria,Shitara, Hiroaki,Yasutake, Mikio,Sakurai, Rumiko,Hirose, Takuji
, p. 326 - 332 (2011)
Solvent-induced chirality control in the enantioseparation of 1-phenylethylamine 1 by N-(p-toluenesulfonyl)-(S)-phenylalanine 2 via diastereomeric salt formation was studied. (S)-·(S)-2 was preferentially crystallized as a less-soluble salt from aqueous a
Amplification of the enantiomeric excess of a compound in kinetic resolution by a racemic reagent
Satyanarayana, Tummanapalli,Kagan, Henri B.
, p. 6415 - 6422 (2007)
The possibility of amplifying the small ee of a enantioimpure substance using a racemic reagent in kinetic resolution is discussed. A kinetic treatment of this problem along with some experimental proofs of the concept is presented. Simulation on kinetic resolution of small ee substrate by a racemic reagent showed an important enantioenrichment in the substrate ee, sometimes reaching close to absolute ee. Experiments of kinetic resolution of an amine of a small ee by a racemic acylating reagent gave a substantial amplification in ee of the amine. The possible transformation of an undetectable low ee in substrate to a detectable higher ee by using a suitable racemic reagent is also briefly discussed with help of calculations. The usefulness of asymmetric amplification by a racemic reagent is considered in the context of the biomolecular homochirality on earth.
Ph-tetrame-bithienine, the first member of the class of chiral heterophosphepines: Synthesis, electronic and steric properties, metal complexes and catalytic activity
Vaghi, Luca,Benincori, Tiziana,Cirilli, Roberto,Alberico, Elisabetta,Mussini, Patrizia Romana,Pierini, Marco,Pilati, Tullio,Rizzo, Simona,Sannicolo, Francesco
, p. 8174 - 8184 (2013)
Unknown 1H-2,7-dihydro-1-phenylphosphepine, containing a 2,2,5,5-tetramethyl-3,3-bithiophene atropisomeric scaffold (Ph-tetraMe- Bithienine), and its oxide have been synthesized and structurally characterized by single-crystal X-ray diffraction analysis.
Chiroptical Asymmetric Reaction Screening via Multicomponent Self-Assembly
De Los Santos, Zeus A.,Wolf, Christian
, p. 13517 - 13520 (2016)
Self-assembly of a stereodynamic phosphine ligand, Pd(II), and a chiral amine, amino alcohol, or amino acid generates characteristic UV and CD signals that can be used for quantitative stereochemical analysis of the bound substrate. A robust mix-and-measure chiroptical sensing protocol has been developed and used to determine the absolute configuration, ee, and yield of an amine produced by Ir-catalyzed asymmetric hydrogenation of an iminium salt. The analysis requires only 1 mg of the crude reaction mixture and minimizes cost, labor, time, and waste.
Unprecedented, fully recyclable, solid-supported reagent for the kinetic resolution of racemic amines through enantioselective N-acetylation
Arseniyadis, Stellios,Subhash, Pithani V.,Valleix, Alain,Wagner, Alain,Mioskowski, Charles
, p. 3310 - 3312 (2005)
The high-yielding synthesis and application of the first polymer supported reagent for the kinetic resolution (KR) of amines through enantioselective acetylation is described; this new supported chiral reagent allows the KR of primary amines with excellent selectivities at room temperature; moreover, this supported approach is highly efficient as the Merrifield-supported chiral scaffold can be quantitatively recovered and recycled. The Royal Society of Chemistry 2005.
A new benchmark for the non-enzymatic enantioselective acylation of amines: Use of a planar-chiral derivative of 4-pyrrolidinopyridine as the acylating agent
Ie, Yutaka,Fu, Gregory C.
, p. 119 - 120 (2000)
N-Acetylated Ph-PPY*, a new planar-chiral derivative of PPY, serves as an effective reagent for the enantioselective acylation of racemic amines, providing amides with very good stereoselectivity.
The application of monodentate secondary phosphine oxide ligands in rhodium- and iridium-catalyzed asymmetric hydrogenation
Jiang, Xiao-Bin,Van Den Berg,Minnaard, Adriaan J.,Feringa, Ben L.,De Vries, Johannes G.
, p. 2223 - 2229 (2004)
Enantiopure secondary phosphine oxides have been tested as ligands in the rhodium- and iridium-catalyzed asymmetric hydrogenation of functionalized olefins. tert-Butylphosphinoyl benzene turned out to be a versatile ligand in the iridium-catalyzed hydroge
Rhodium-catalyzed asymmetric olefin hydrogenation by easily accessible aniline- and pyridine-derived chiral phosphites
Vallianatou, Kalliopi A.,Frank, Dominik J.,Antonopoulou, Georgia,Georgakopoulos, Spyros,Siapi, Eleni,Zervou, Maria,Kostas, Ioannis D.
, p. 397 - 401 (2013)
An aniline- and two pyridine-derived (R)-BINOL-based P,N-containing phosphite ligands have been synthesized via a one-pot procedure. Treatment of the aniline-derived ligand with 1 equiv of [Rh(COD)2]BF4 yielded a mixture of a P,N-che
Asymmetric hydrogenation of enamides, α-enol and α-enamido ester phosphonates catalyzed by IndolPhos-Rh complexes
Wassenaar, Jeroen,Reek, Joost N. H.
, p. 8403 - 8406 (2009)
(Chemical Equation Presented) The scope of the IndolPhos-Rh-catalyzed asymmetric hydrogenation of enamides, α-enol and α-enamido ester phosphonates, has been investigated. In addition, Taddol-based IndolPhos ligands are introduced. High activities and goo
Asymmetric Induction via Co-ordination to Cr(CO)3; Nucleophilic Attack on Acyclic Carbenium Ions
Top, Siden,Jaouen, Gerard,McGlinchey, Michael J.
, p. 1110 - 1112 (1980)
Temporary complexation of (S)-(-)-1-phenylethanol by the Cr(CO)3 moiety allows the use of carbenium ions to bring about asymmetric transformations with a high degree of retention of configuration, even in open-chain compounds.
