138258-79-4Relevant academic research and scientific papers
Mechanistic and Synthetic Studies in Catalytic Allylic Alkylation with Palladium Complexes of 1-(2-Diphenylphosphino-1-naphthyl)isoquinoline
Brown, John M.,Hulmes, David I.,Guiry, Patrick J.
, p. 4493 - 4506 (1994)
The title complexes are highly reactive catalysts for the reaction between (E)-1,3-diphenyl-2-propenyl acetate and dimethyl malonate ion; the enantiomer excess varies between 67percent and 98percent depending on how the reaction is conducted, with the best result obtained in CH3CN at -13 deg C in the presence of 15-crown-5.With 2-cyclohexyl acetate the reaction was much slower and the best e.e. obtained was 67percent.With 1,1,3-triphenyl-2-propenyl acetate, reaction was again much slower than in the first case, the best e.e. was 47percent, and the configurational correlation between catalyst and reactant was in the opposite sense.Many of the trends can be satisfatorily rationalised by recourse to the NMR spectra of a series of Pd allyl complexes.In the case of the (E,E)-1,3-diphenylallyl complexe, two diastereomers were observed and their configurations assigned with the aid of nOe experiments.The results are best interpreted if the reaction proceeds through a late transition-state with nucleophilic attack on the allyl trans- to the phosphorous of the ligand and preferentially on the predominant diastereomer.
New highly effective phosphite-phosphoramidite ligands for palladium-catalysed asymmetric allylic alkylation reactions
Pamies, Oscar,Dieguez, Montserrat,Claver, Carmen
, p. 836 - 840 (2007)
We have designed a new family of readily I available highly-modular phosphite-phosphoramidite ligands for asymmetric allylic aJkylation reactions. The introduction of a phosphoramidite moiety in the ligand design is highly advantageous in the product outcome. Thus, this ligand series affords high reaction rates and enantioselectivities and, at the same time, shows a broad scope for disubstituted hindered and unhindered substrate types.
Sugar-based diphosphoroamidite as a promising new class of ligands in Pd-catalyzed asymmetric allylic alkylation reactions
Raluy, Eva,Dieguez, Montserrat,Pamies, Oscar
, p. 2842 - 2850 (2007)
(Chemical Equation Presented) We have designed a new family of readily available modular diphosphoroamidite ligands from D-xylose for Pd-catalyzed asymmetric allylic alkylation reactions. This constitutes the first example of diphosphoroamidite ligands ap
New homochiral phosphine ligands having a hexahydro-1H-pyrrolo[1,2-c]imidazolone backbone: Preparation and use for palladium-catalyzed asymmetric alkylation of cycloalkenyl carbonates
Shibatomi, Kazutaka,Uozumi, Yasuhiro
, p. 1769 - 1772 (2002)
New chiral ligands having a pyrrolo[1,2-c]imidazolone backbone were prepared by condensation of anilides of homochiral cyclic amino acids with 2-(diphenylphosphino)benzaldehyde. Of these ligands, (3R,9aS)-(3-(2-diphenylphosphino)phenyl-2-phenyl)tetrahydro-1H-imidazo [1,5-a]indole-1-one was found to be effective for palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl carbonates with dimethyl malonate to give the corresponding dimethyl cycloalkenylmalonates with e.e. of up to 89%.
Synthesis of novel P-ketimine bidentate ferrocenyl ligands with central and planar chirality and comparsion in the catalytic activity between P-ketimine and P-aldimine
Hu, Xiangping,Chen, Huilin,Dai, Huicong,Zheng, Zhuo
, p. 3415 - 3421 (2003)
A series of novel ferrocenylphosphine-ketimine ligands 6 were prepared by reaction of (R,Sp)-PPFNH2-R or (S,Sp)- PPFNH2 with a variety of m-substituted acetophenones. A different catalytic activity was observed
A new, chiral bis-benzothiazine ligand
Harmata, Michael,Ghosh, Sunil K.
, p. 3321 - 3323 (2001)
Equation presented The synthesis and application of a new, chiral bis-benzothiazine ligand are described.
C2-symmetric diphosphine ligands with only the planar chirality of ferrocene for the palladium-catalyzed asymmetric allylic alkylation
Zhang, Wanbin,Shimanuki, Takashi,Kida, Toshiyuki,Nakatsuji, Yohji,Ikeda, Isao
, p. 6247 - 6251 (1999)
Novel C2-symmetric diphosphine ligands possessing only the planar chirality of ferrocene, 1,1'-bis(diphenylphosphino)-2,2'-disubstituted- ferrocenes, were prepared from 1,1'-bis(diphenylphosphino)-2,2'- bis(oxazolinyl)ferrocene by the transform
Chiral phosphinooxazolines with a pentamethylferrocene backbone - Synthesis and use as ligands in asymmetric catalysis
Geisler, Felix M.,Helmchen, Guenter
, p. 2486 - 2492 (2006)
Novel phosphinooxazolines, containing a unit of central and a unit of planar chirality in a matched case combination, have been successfully tested in the Pd-catalyzed asymmetric allylic substitution with cycloalkenyl acetates as substrates.
Mechanistic implications of the observation of kinetic resolution in a palladium-catalyzed enantioselective allylic alkylation
Ramdeehul, Shailesh,Dierkes, Peter,Aguado, Rafael,Kamer, Paul C. J.,Van Leeuwen, Piet W. N. M.,Osborn, John A.
, p. 3118 - 3121 (1998)
Preferential rotation in substrate-palladium intermediates in a catalyzed asymmetric allylic alkylation is proposed to be responsible for both the observed kinetic resolution of the racemic allylic acetate starting material as well as the high selectivity
Chiral wide-bite-angle diphosphine ligands: Synthesis, coordination chemistry, and application in Pd-catalyzed allylic alkylation
Czauderna, Christine F.,Jarvis, Amanda G.,Heutz, Frank J.L.,Cordes, David B.,Slawin, Alexandra M.Z.,Van Der Vlugt, Jarl Ivar,Kamer, Paul C.J.
, p. 1608 - 1618 (2015)
A series of diphosphine ligands bearing ester- and ether-modified diphenylether backbones have been prepared. The introduction of carboxylic acid or ether auxiliaries in the ortho-positions relative to the diphenylphosphine groups was achieved via straigh
