131065-36-6Relevant articles and documents
Chiral amido- and diamidophosphites with a peripheral pyridine ring in Pd-catalyzed asymmetric allylation
Gavrilov,Zheglov,Novikov,Gavrilov,Zamilatskov,Mikhel
, p. 2278 - 2285 (2016)
New chiral amidophosphite and diamidophosphite ligands with exocyclic pyridyl-containing substituents were obtained. Their efficiency in the Pd-catalyzed enantioselective allylic substitution was compared: in the sulfonylation of (E)-1,3-diphenylallyl ace
New chiral chelating phosphine complexes containing tricarbonyl(η6-arene) chromium for highly enantioselective allylic alkylation
Hayashi, Yoshinori,Sakai, Hiroshi,Kaneta, Naotake,Uemura, Motokazu
, p. 143 - 148 (1995)
New chiral phosphine complexes with an additional chelating group containing tricarbonyl(η6-arene)chromium were prepared from (R)-1-phenylethylamine and (S)-1-phenylethanol.Catalytic asymmetric alkylation of 1,3-diphenyl-1-acetoxypropene with sodium dimethyl malonate in the presence of palladium(0) catalyst with the chiral (arene)chromium complexes gave the alkylation product of up to 94percent ee.Keywords: (Arene)chromium; Chiral phosphine ligand; Planar chirality; Catalysis; Allylic alkylation
Synthetic and mechanistic studies in enantioselective allylic substitutions catalysed by palladium complexes of a modular class of axially chiral quinazoline-containing ligands
Carroll, Anne-Marie,McCarthy, Mary,Lacey, Patrick M.,Saunders, Cormac P.,Connolly, David J.,Farrell, Annette,Rokade, Balaji V.,Goddard, Richard,Fristrup, Peter,Norrby, Per-Ola,Guiry, Patrick J.
, (2020)
The application of palladium complexes of a modular series of axially chiral phosphinamine ligands, the Quinazolinaps, to the enantioselective alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate and methyl dimethyl malonate is described.
Homogeneous and Heterogeneous Pd-catalyzed Enantioselective Alkylation with C2-symmetric Chiral Nitrogen Ligands
Gamez, Patrick,Dunjic, Branko,Fache, Fabienne,Lemaire, Marc
, p. 1109 - 1116 (1995)
Several allylic acetates have been enantioselectively substituted by alkylation using (C2-symmetric chiral diamine)-Pd complexes or (pseudo C2-symmetric chiral polymer)-Pd complexes with up to 95percent and 80percent ee respectively.
Asymmetric allylic alkylation catalyzed by Pd(II)-complexes with (S)-BINPO, a hemilabile axially chiral P,O-heterodonor inducer
Gladiali, Serafino,Taras, Rossana,Ceder, Rosa M.,Rocamora, Merce,Muller, Guillermo,Solans, Xavier,Font-Bardia, Merce
, p. 1477 - 1485 (2004)
A complex generated in situ from [Pd(η3-C3H 5)Cl]2 and (S)-BINPO 1 is an active catalyst in the asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl esters 6 via a malonate anion with ee's up to 81% being obtained. Rate and stereoselectivity of the reaction are dramatically influenced by the solvent. The Pd-complex [(S)-(BINPO)Pd(η3-1,3-diphenylallyl)] 5has been synthesized and its structure in the solid state determined by X-ray diffraction. The stoichiometric reaction of 5 with malonate anion affords the alkylated product of the same configuration as the one obtained in the catalytic reaction at room temperature in nearly identical enantiomeric purity (71%).
Enantioselective synthesis of planar chiral ferrocenes via palladium-catalyzed annulation with diarylethynes
Shi, Yan-Chao,Yang, Rong-Fei,Gao, De-Wei,You, Shu-Li
, p. 1891 - 1896 (2013)
When Boc-L-Val-OH was used as a ligand for the enantioselective Pd(II)-catalyzed annulation of N,N-substituted aminomethyl ferrocene derivatives with diarylethynes, ferrocenes with planar chirality could be achieved with excellent enantioselectivity (up to 99% ee).
Novel axial chiral sulfur-oxazoline ligands with a biphenyl backbone
Imai, Yoshitane,Zhang, Wanbin,Kida, Toshiyuki,Nakatsuji, Yohji,Ikeda, Isao
, p. 1319 - 1321 (1999)
A novel axial chiral sulfur-oxazoline ligand with a biphenyl backbone 3 exists as a mixture of two diastereomers in equilibrium in solution. However, when this ligand was coordinated with palladium(II), only one of the two possible diastereomeric complexe
New Ligands for Asymmetric Palladium Catalysed Allylic Substitution Reactions. X-ray Crystal Structures of Two Enantiomerically Pure Dihydrobenzazaphosphole-Borane Complexes.
Brenchley, Guy,Fedouloff, Michael,Mahon, Mary F.,Molloy, Kieran C.,Wills, Martin
, p. 10581 - 10592 (1995)
The synthesis, application and X-ray crystal structures of two enantiomerically pure dihydrobenzazaphosphole-borane complexes, precursors of ligands for highly enantioselective palladium catalysed allylic substitution reactions, are described.The structur
C2-symmetric bisphosphinobioxazoline as a chiral ligand. Highly enantioselective palladium-catalyzed allylic substitutions and formation of P,N,N,P tetradentate palladium (II) complexes
Lee, Sang-Gi,Lim, Chung Woo,Song, Choong Eui,Kim, Kwan Mook,Jun, Chul Ho
, p. 4445 - 4451 (1999)
The C2-symmetric bisphosphinobioxazoline [(S,S)-Phos-Biox] 4 was found to be a highly efficient chiral ligand for Pd-catalyzed enantioselective allylic substitution of rac-1,3-diphenyl-2-propenyl acetate with dimethyl malonate and afforded enantioselectivities of up to 97% ee. Moderate enantioselectivities have been observed in Pd-catalyzed desymmetrizations of cis-1,4-bis(benzoyloxy)-cyclopent-2-ene (12) with dimethyl malonate (51-78% yield, 38-58% ee) and N-benzyl-N-methylamine (87% yield, 33% ee) nucleophiles and of biscarbamate 15 of cis-1,4-dihydroxycyclopent-2-ene (90% yield, 50% ee). A 1:1 molar mixture of (S,S)-Phos-Biox 4 with Pd(CH3CN)2Cl2 and (η3-C3H5)PdCl]2 afforded the P,N,N,P-tetradentate Pd(II) complexes 19a and 19b, respectively. The structures of the complexes 19a, b were determined by X-ray analysis. The complex 19a also exhibited high enantioselectivity (86% yield, 92% ee) in allylic substitution of rac-1,3-diphenyl-2-propenyl acetate with dimethyl malonate.
Diastereomeric P*-chiral diamidophosphites with terpene fragments in asymmetric catalysis
Gavrilov, Konstantin N.,Benetsky, Eduard B.,Grishina, Tatiana B.,Zheglov, Sergey V.,Rastorguev, Eugenie A.,Petrovskii, Pavel V.,Macaev, Fliur Z.,Davankov, Vadim A.
, p. 2557 - 2564 (2007)
Diamidophosphite P*-monodentate, ligands based on terpene alcohols and (S)- or (R)-(2-anilinomethyl)pyrrolidine, induce high enantioselectivities (ee's up to 99%) in Pd-catalyzed allylic substitution reactions. In the Pd-catalyzed deracemizatio
