Online citations, reference lists, and bibliographies.
← Back to Search

P-Chirogenic Phosphines Supported By Calix[4]arene: New Insight Into Palladium-Catalyzed Asymmetric Allylic Substitution

Naima Khiri-Meribout, E. Bertrand, Jérôme Bayardon, Marie-Joëlle Eymin, Yoann Rousselin, H. Cattey, D. Fortin, P. Harvey, S. Jugé
Published 2013 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
The first P-chirogenic mono- and diphosphine ligands supported on the upper rim of a calix[4]arene moiety were synthesized using the ephedrine methodology. The lithiated calix[4]arene mono- and dianions both react with the oxazaphospholidine–borane, prepared from ephedrine, to afford regio- and stereoselectively the corresponding calix[4]arenyl aminophosphine–boranes, by cleavage of the heterocyclic ring at the P–O bond position. Subsequent reactions with HCl and then organolithium reagent and finally decomplexation with DABCO lead to the corresponding calix[4]arenyl mono- or diphosphines. Both enantiomers of the calix[4]arenyl phosphines were obtained either by using (+)- or (−)-ephedrine or by changing the addition order of the organolithium reagents during the synthesis. The enantiomeric excesses of the phosphines were determined either by HPLC on a chiral column of their borane complexes or by 31P NMR in the presence of a chiral palladium complex. The absolute configurations of the mono- and diphosphi...
This paper references
10.1002/JCC.540070313
Molecular orbital theory of the properties of inorganic and organometallic compounds 4. Extended basis sets for third‐and fourth‐row, main‐group elements
K. Dobbs (1986)
10.1039/B204604K
Heterofunctionalised phosphites built on a calix[4]arene scaffold and their use in 1-octene hydroformylation. Formation of 12-membered P,O-chelate rings
S. Steyer (2002)
10.1002/EJOC.200600966
Modular P-Chirogenic Aminophosphane-Phosphinite Ligands for Rh-Catalyzed Asymmetric Hydrogenation: A New Model for Prediction of Enantioselectivity
C. Darcel (2007)
10.1002/EJIC.200700764
Chiral Calix[4]arene-Based Diphosphites as Ligands in the Asymmetric Hydrogenation of Prochiral Olefins
A. Marson (2007)
10.1021/ja9045839
Catalytic asymmetric synthesis of chiral tertiary organoboronic esters through conjugate boration of beta-substituted cyclic enones.
I-Hon Chen (2009)
10.1021/OM100520U
Enantioselective Hydrogenation Catalysis Aided by a σ-Bonded Calix[4]arene to a P-Chirogenic Aminophosphane Phosphinite Rhodium Complex†
Naïma Khiri (2010)
10.1016/J.CRCI.2008.01.008
Influence des propriétés intrinsèques de ligands calixaréniques sur des réactions de transformation catalytique de l'éthylène
David Sémeril (2008)
10.1002/ADSC.200303138
The Development of Bidentate P,N Ligands for Asymmetric Catalysis
P. Guiry (2004)
10.1039/c0cc05805j
High efficiency of cavity-based triaryl-phosphines in nickel-catalysed Kumada-Tamao-Corriu cross-coupling.
L. Monnereau (2011)
10.1021/ic802253t
Replacement of a nitrogen by a phosphorus donor in biomimetic copper complexes: a surprising and informative case study with calix[6]arene-based cryptands.
D. Over (2009)
10.1021/JA00466A020
Chiral metal complexes. 4. Resolution of racemic tertiary phosphines with chiral palladium(II) complexes. The chemistry of diastereomeric phosphine palladium(II) species in solution
K. Tani (2002)
10.1002/1099-0682(200012)2000:12<2523::AID-EJIC2523>3.0.CO;2-G
η1‐ and η3‐Allylpalladium(II) Complexes Bearing Potentially Tridentate Ligands: Synthesis, Solution Dynamics, and Crystal Structures
L. Barloy (2000)
10.1021/ja209700j
Rigid P-chiral phosphine ligands with tert-butylmethylphosphino groups for rhodium-catalyzed asymmetric hydrogenation of functionalized alkenes.
T. Imamoto (2012)
10.1016/0009-2614(89)87234-3
Results obtained with the correlation energy density functionals of becke and Lee, Yang and Parr
B. Miehlich (1989)
10.1103/PHYSREVB.37.785
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.
Lee (1988)
10.1021/OM980754A
Ferrocenyl Diphosphines Containing Stereogenic Phosphorus Atoms. Synthesis and Application in the Rhodium-Catalyzed Asymmetric Hydrogenation
Francesca Maienza (1999)
10.1021/JA076634O
Copper-catalyzed enantioselective substitution of allylic carbonates with diboron: an efficient route to optically active alpha-chiral allylboronates.
H. Ito (2007)
10.1002/ADSC.200900074
Micellar Effects in Olefin Hydroformylation Catalysed by Neutral, Calix[4]arene‐Diphosphite Rhodium Complexes
L. Monnereau (2009)
10.1002/ANIE.201106864
Cover Picture: A Diagonal Approach to Chemical Recycling of Carbon Dioxide: Organocatalytic Transformation for the Reductive Functionalization of CO2 (Angew. Chem. Int. Ed. 1/2012)
C. Gomes (2012)
10.1002/HC.1088
Synthesis of new calix[4]arene‐based phosphorus ligands and their application in the Rh(I) catalyzed hydroformylation of 1‐octene
C. Kunze (2001)
10.1002/9781118299715
Phosphorus(III) ligands in homogeneous catalysis : design and synthesis
P. Kamer (2012)
10.1021/ol101936w
Enantiopure 1,2-bis(tert-butylmethylphosphino)benzene as a highly efficient ligand in rhodium-catalyzed asymmetric hydrogenation.
K. Tamura (2010)
10.1021/ol101029s
Impact on hydrogenation catalytic cycle of the R groups' cyclic feature in "R-SMS-Phos".
B. Zupancic (2010)
10.1016/J.TETASY.2005.05.039
Synthesis of calix[4]arene derivatives bearing chiral pendant groups as ligands for enantioselective catalysis
C. Gaeta (2005)
10.1103/PHYSREV.140.A1133
Self-Consistent Equations Including Exchange and Correlation Effects
W. Kohn (1965)
10.1021/ja00374a017
Self-consistent molecular-orbital methods. 22. Small split-valence basis sets for second-row elements
M. Gordon (1980)
10.1002/ANIE.200601978
Regioselectivity with hemispherical chelators: increasing the catalytic efficiency of complexes of diphosphanes with large bite angles.
David Sémeril (2006)
10.1016/J.TETASY.2006.02.008
Highly enantioselective hydrosilylation of simple ketones catalyzed by rhodium complexes of P-chiral diphosphine ligands bearing tert-butylmethylphosphino groups
T. Imamoto (2006)
10.1039/A909103C
Calix[4]arene based monophosphites, identification of three conformations and their use in the rhodium-catalysed hydroformylation of 1-octene
F. Parlevliet (2000)
10.1039/c2cs35410a
Rhodium-catalysed asymmetric hydrogenation as a valuable synthetic tool for the preparation of chiral drugs.
Pablo Etayo (2013)
10.1039/B009005K
Calix[4]arene-derived diphosphines, diphosphinites and diphosphites as chelating ligands for transition metal ions. Encapsulation of silver(I) in a calix-crown diphosphite
C. Jeunesse (2001)
10.1021/JA00383A007
Self-consistent molecular orbital methods. 24. Supplemented small split-valence basis sets for second-row elements
William J. Pietro (1982)
10.1021/JA053458F
An air-stable P-chiral phosphine ligand for highly enantioselective transition-metal-catalyzed reactions.
T. Imamoto (2005)
10.1021/cr8002196
The use of calixarenes in metal-based catalysis.
Damien M. Homden (2008)
10.1021/ja905908z
Rhodium-catalyzed highly enantioselective direct intermolecular hydroacylation of 1,1-disubstituted alkenes with unfunctionalized aldehydes.
Yu Shibata (2009)
10.1063/1.464913
Density-functional thermochemistry. III. The role of exact exchange
Axel D. Becke (1993)
10.1107/S0021889892010331
Completion and refinement of crystal structures with SIR92
A. Altomare (1993)
10.1107/S0108767307043930
A short history of SHELX.
G. Sheldrick (2008)
10.1021/ja076542z
Asymmetric hydrogenation catalyzed by a rhodium complex of (R)-(tert-butylmethylphosphino)(di-tert-butylphosphino)methane: scope of enantioselectivity and mechanistic study.
I. Gridnev (2008)
10.1016/S0957-4166(97)00300-5
ortho-palladated α-phenylalkylamines for enantiomeric purity determination of monodentate P∗-chiral phosphines
V. V. Dunina (1997)
10.1016/S0076-6879(97)76066-X
[20] Processing of X-ray diffraction data collected in oscillation mode.
Z. Otwinowski (1997)
10.1021/CR020049I
New chiral phosphorus ligands for enantioselective hydrogenation.
Wenjun Tang (2003)
10.1039/b907100h
Calixarene-monophosphines as supramolecular chelators.
Soheila Sameni (2009)
10.1039/P19830001009
Base catalysed rearrangements involving ylide intermediates. Part 15. The mechanism of the Stevens [1,2] rearrangement
W. Ollis (1983)
10.1016/J.CCR.2012.10.006
Metallated cavitands (calixarenes, resorcinarenes, cyclodextrins) with internal coordination sites
Rafael Gramage-Doria (2013)
10.1016/J.JORGANCHEM.2008.03.008
Phosphite ligands derived from distally and proximally substituted dipropyloxy calix[4]arenes and their palladium complexes: Solution dynamics, solid-state structures and catalysis
A. Sarkar (2008)
10.1021/JO0264123
P-chiral, monodentate ferrocenyl phosphines, novel ligands for asymmetric catalysis.
Elizabeth A. Colby (2003)
10.1039/A908961F
Rhodium(I) complexes of robust phosphites derived from calix[4]arenes and their application in the hydroformylation of 1-hexene
Christopher J. Cobley (2000)
10.1021/JA00523A008
Self-consistent molecular orbital methods. 21. Small split-valence basis sets for first-row elements
J. Binkley (2002)
10.1139/V92-085
Relativistic compact effective potentials and efficient, shared-exponent basis sets for the third-, fourth-, and fifth-row atoms
W. Stevens (1992)
10.1021/JO026355D
Highly enantiomerically enriched chlorophosphine boranes: synthesis and applications as P-chirogenic electrophilic blocks.
C. Bauduin (2003)
10.1021/JO071192K
t-Bu-QuinoxP* ligand: applications in asymmetric Pd-catalyzed allylic substitution and Ru-catalyzed hydrogenation.
T. Imamoto (2007)
10.1021/OM800969Z
Synthesis, Structures, and Photoluminescent Properties of Cyclometalated Platinum(II) Complexes bearing Upper-Rim Phosphinated Calix[4]arenes
Siu-Wai Lai (2009)
10.1016/J.CRCI.2010.06.001
Enantiodivergent synthesis of P-chirogenic phosphines
F. Chaux (2010)
10.1021/OL0258637
Recognition and catalysis in allylic alkylations.
C. Gibson (2002)
10.1021/JO982481Z
Phosphorous-chiral analogues of 1,1'-Bis(diphenylphosphino)ferrocene: Asymmetric synthesis and application in highly enantioselective rhodium-catalyzed hydrogenation reactions
U. Nettekoven (1999)
10.1039/B102371N
Rhodium-catalyzed biphasic hydroformylation of 4-octene using water-soluble calix[4]arene-phosphine ligands
S. Shirakawa (2001)
10.1002/(SICI)1521-3773(19990712)38:13/14<1920::AID-ANIE1920>3.0.CO;2-C
Chelated Bisphosphites with a Calix[4]arene Backbone: New Ligands for Rhodium‐Catalyzed Low‐Pressure Hydroformylation with Controlled Regioselectivity
R. Paciello (1999)
10.1002/chem.200903390
Cavity-shaped ligands: calix[4]arene-based monophosphanes for fast Suzuki-Miyaura cross-coupling.
L. Monnereau (2010)
10.1002/ANIE.200702513
Synthesis and enantioselectivity of p-chiral phosphine ligands with alkynyl groups.
T. Imamoto (2007)
10.1016/S0957-4166(03)00439-7
A novel P-chirogenic phosphine ligand, (S, S)-1,2-bis-[(ferrocenyl)methylphosphino]ethane: synthesis and use in rhodium-catalyzed asymmetric hydrogenation and palladium-catalyzed asymmetric allylic alkylation
Nobuhiko Oohara (2003)
10.1021/OM990209P
The synthesis of a calix[6]arene derived diphosphate, its palladium and platinum complexes and the remarkable activity of (syn-calix[6]arene diphophate)Pd(CH3)(CH3CN)OTf in carbon monoxide and ethene copolymerisation
F. Parlevliet (1999)
10.1021/OP2002613
Allylic Amines as Key Building Blocks in the Synthesis of (E)-Alkene Peptide Isosteres.
Erin M. Skoda (2012)
10.1039/B101369F
Diphosphines based on an inherently chiral calix[4]arene scaffold: synthesis and use in enantioselective catalysis
Cedric B. Dieleman (2001)
10.1002/chem.200800747
Highly regioselective hydroformylation with hemispherical chelators.
David Sémeril (2008)
10.1021/OM050421V
Allylpalladium Complexes with P-Stereogenic Monodentate Phosphines. Application in the Asymmetric Hydrovinylation of Styrene
A. Grabulosa (2005)
10.1103/PHYSREV.136.B864
THE INHOMOGENEOUS ELECTRON GAS.
P. Hohenberg (1964)
10.1002/ADSC.200390031
Recent Developments in Catalytic Asymmetric Hydrogenation Employing P‐Chirogenic Diphosphine Ligands
Karen V. L. Crepy (2003)
10.1021/OM020323Z
An (η1-Allyl)palladium Complex of a Chiral Bidentate Ligand: Crystallographic and NMR Studies on a (η1-3,3-Diphenylallyl)(phosphinooxazoline)palladium Complex
Martin Kollmar† and (2002)
10.1021/ol900533h
Optically active dinuclear palladium complexes containing a Pd-Pd bond: preparation and enantioinduction ability in asymmetric ring-opening reactions.
T. Ogura (2009)
10.1039/A905814A
Co-ordination chemistry of macrocyclic compounds with dangling phosphines. Unusual NMR shifts in metallo-calix[4]arenes†
Cedric B. Dieleman (1999)
10.1016/S0022-328X(98)00837-7
Carbonylation (hydroformylation and hydrocarbalkoxylation) reactions in the presence of transition metal: p-tert-butyl-calix[4]arene-based phosphine and phosphinite systems
Zsolt Csók (1998)
10.1021/JA048496Y
Highly selective asymmetric hydrogenation using a three hindered quadrant bisphosphine rhodium catalyst.
Garrett S Hoge (2004)
10.1021/OM000433A
(η5-Pentamethylcyclopentadienyl)rhodium Complexes of Upper-Rim Monophosphinated Calix[4]arene
M. Vezina (2001)
10.2174/157019309789371640
Design and synthesis of transition metal and inner transition metal binding calixarenes
S. Siddiqui (2009)
10.1002/HLCA.200390109
Chiral and Achiral Crystal Structures
H. Flack (2003)
10.1039/B110884K
Positioning of transition metal centres at the upper rim of cone-shaped calix[4]arenes. Filling the basket with an organometallic ruthenium unit
M. Lejeune (2002)
10.1002/3527602151
Asymmetric Catalysis on Industrial Scale
H. Blaser (2003)
10.1039/c0cc02620d
Design and synthesis of a novel three-hindered quadrant bisphosphine ligand and its application in asymmetric hydrogenation.
Kexuan Huang (2010)
10.1002/JCC.540080614
Molecular orbital theory of the properties of inorganic and organometallic compounds 5. Extended basis sets for first‐row transition metals
K. Dobbs (1987)
10.1063/1.447604
Compact effective potentials and efficient shared‐exponent basis sets for the first‐ and second‐row atoms
W. Stevens (1984)
10.1107/S0108767383001762
On enantiomorph‐polarity estimation
H. Flack (1983)
10.1107/S0021889800007184
Reporting and evaluating absolute-structure and absolute-configuration determinations
H. Flack (2000)
10.1021/AR030156E
On the mechanism of stereoselection in Rh-catalyzed asymmetric hydrogenation: a general approach for predicting the sense of enantioselectivity.
I. Gridnev (2004)
10.1021/OM030095O
Syntheses and Characterization of Upper Rim 1,2- and 1,3-Diphosphinated Calix[4]arenes and Their Corresponding 1,5-Cyclooctadienylrhodium(I) Complexes: Comparison of the Catalytic Hydroformylation Properties of Terminal Alkenes
François Plourde (2003)
10.1039/c2cs15312b
Asymmetric homogeneous hydrogenations at scale.
David J. Ager (2012)
10.1007/978-94-009-9027-2_2
Density-functional theory of atoms and molecules
R. Parr (1989)
10.1021/JA00842A058
Asymmetric hydrogenation with a complex of rhodium and a chiral bisphosphine
W. Knowles (1975)
10.1107/S0021889897003117
ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI)
L. Farrugia (1997)
10.1063/1.464902
Effective core potential methods for the lanthanides
T. Cundari (1993)
10.1002/9781118299715.CH12
P‐Chiral Ligands
Jérôme Bayardon (2012)
10.1039/b912440c
Mechanism of enantioselection in Rh-catalyzed asymmetric hydrogenation. The origin of utmost catalytic performance.
I. Gridnev (2009)
10.1016/S0022-328X(96)06690-9
Asymmetric synthesis of (S,S)-(+)-1,1′-bis-(methyl-phenyl-phosphino) ferrocene
El Bachir Kaloun (1997)
10.1021/JO001175U
Steric and electronic ligand perturbations in catalysis: asymmetric allylic substitution reactions using C2-symmetrical phosphorus-chiral (bi)ferrocenyl donors.
U. Nettekoven (2001)
10.1021/BK-1989-0394
The Challenge of d and f electrons : theory and computation
D. Salahub (1989)
10.1002/anie.201004041
Primary and secondary aminophosphines as novel P-stereogenic building blocks for ligand synthesis.
Marc Reves (2010)



This paper is referenced by
10.1016/J.TETLET.2015.08.010
Reversible nucleophilic addition can lower the observed enantioselectivity in palladium-catalyzed allylic amination reactions with a variety of chiral ligands
Nicholas S. Caminiti (2015)
10.1039/c3dt52550c
Novel chiral (salen)Mn(III) complexes containing a calix[4]arene unit in 1,3-alternate conformation as catalysts for enantioselective epoxidation reactions of (Z)-aryl alkenes.
C. Bonaccorso (2014)
10.1080/10426507.2014.999368
Designing P*-chirogenic Organophosphorus Compounds: from Ligands to Organocatalysts
S. Jugé (2015)
10.1016/J.CCR.2014.06.019
Synthesis and catalytic relevance of P(III) and P(V)-functionalised calixarenes and resorcinarenes
David Sémeril (2014)
10.1021/ACS.ORGANOMET.5B00999
Pd(II) Complexes Ligated by 1,3-Bis(diphenylphosphino)calix[4]arene: Preparation, X-ray Structures, and Catalyses
Kengo Hirasawa (2016)
10.1039/c5cc03517a
A one-step, modular route to optically-active diphos ligands.
E. Louise Hazeland (2015)
10.1016/J.TETLET.2016.12.049
Ligand and base additive effects on the reversibility of nucleophilic addition in palladium-catalyzed allylic aminations monitored by nucleophile crossover
Bryan S. Holtzman (2017)
10.1002/EJOC.201600208
Chiral Phosphinoferrocenyl‐Calixarenes
Andrii Karpus (2016)
10.1039/c3dt52412d
Ni(II) tetraphosphine complexes as catalysts/initiators in the ring opening polymerization of ε-caprolactone.
Xin-Yi Wu (2014)
10.1039/d0dt01204a
An iron variant of the Noyori hydrogenation catalyst for the asymmetric transfer hydrogenation of ketones.
Shangfei Huo (2020)
10.1039/C6CS00031B
Applications and stereoselective syntheses of P-chirogenic phosphorus compounds.
Mathieu Dutartre (2016)
Semantic Scholar Logo Some data provided by SemanticScholar