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

RESOLUTION OF BENZYLCYCLOHEXYLPHENYLPHOSPHINE BY PALLADIUM(II)-AMINE METALLACYCLES. A NEW LIGAND FOR ASYMMETRIC HYDROVINYLATION

J. Albert, J. Cadena, J. Granell, G. Muller, J. I. Ordinas, D. Panyella, C. Puerta, Andres Sanudo, P. Valerga
Published 1999 · Chemistry

Save to my Library
Download PDF
Analyze on Scholarcy Visualize in Litmaps
Share
Reduce the time it takes to create your bibliography by a factor of 10 by using the world’s favourite reference manager
Time to take this seriously.
Get Citationsy
The synthesis of benzylcyclohexylphenylphosphine and its resolution by means of optically active palladium metallacycles are reported. The absolute configuration of (RC,SP)-[PdCl(C6H4CHMeNMe2)(PBzCyPh)] has been determined by single-crystal X-ray analyses. The allyl complex [Pd(η3-2-MeC3H4)(PBzCyPh)S]BF4, prepared in situ from [Pd(η3-2-MeC3H4)Cl(PBzCyPh)] and AgBF4 in CH2Cl2 solution, was used as a precatalyst for asymmetric hydrovinylation of styrene and 2-vinylnaphthalene. This system permits the synthesis of 3-phenyl-1-butene and 3-(2-naphthyl)-1-butene with good ee values working in very mild conditions of temperature (15 °C).



This paper is referenced by
10.1021/ACS.ORGANOMET.0C00811
Iridium-Catalyzed Asymmetric Hydroalkenylation of Norbornene Derivatives
Xin-zhi Sun (2021)
10.1002/EJIC.201600608
Neutral and Cationic Palladium Complexes of P‐Stereogenic Phosphanes Bearing a Heterocyclic Substituent
P. Clavero (2016)
10.1039/c6dt00995f
Ruthenium complexes of P-stereogenic phosphines with a heterocyclic substituent.
P. Clavero (2016)
10.1016/J.MOLCATA.2014.04.026
P-Stereogenic monophosphines with the 2-p-terphenylyl and 1-pyrenyl substituents. Application to Pd and Ru asymmetric catalysis
P. Clavero (2014)
10.1016/B978-0-08-097742-3.00533-4
5.32 Hydrovinylation Reactions in Organic Synthesis
T. V. RajanBabu (2014)
10.1002/ADSC.201300864
Highly Efficient Catalytic Dimerization of Styrenes via Cationic Palladium(II) Complexes
J. H. Choi (2013)
10.1002/anie.201303916
Transition-metal-catalyzed laboratory-scale carbon-carbon bond-forming reactions of ethylene.
Vaneet Saini (2013)
10.1002/ANGE.201303916
Übergangsmetallkatalysierte C‐C‐Kupplungen mit Ethylen im Labormaßstab
Vaneet Saini (2013)
10.1039/C3CY00084B
Metal catalysed hydrovinylation
R.Ma. Ceder (2013)
10.1002/EJIC.201101343
Intermolecular Insertion of Dialkynylphosphanes into the M–C Bond of Cyclopalladated Rings through Activation by Cyclometallated Amines
Shuli Chen (2012)
10.1021/ol301935q
Synthesis, reactivity, and resolution of a C2-symmetric, P-stereogenic benzodiphosphetane, a building block for chiral bis(phosphines).
Samantha C. Reynolds (2012)
10.1016/B978-0-08-095167-6.00518-8
5.16 Reduction: Enantioselective Hydrovinylation of Alkenes
T. V. RajanBabu (2012)
10.1039/C2CY00521B
Application of palladium (trioxo-adamantyl cage phosphine)chloride complexes as catalysts for the alkoxycarbonylation of styrene; Pd catalysed tert-butoxycarbonylation of styrene
J. Fuentes (2012)
10.1002/EJOC.201200212
Hydrovinylation Reactions – Atom‐Economic Transformations with Steadily Increasing Synthetic Potential
G. Hilt (2012)
10.1016/J.JORGANCHEM.2011.02.034
P-Stereogenic monophosphines in Pd-catalysed enantioselective hydrovinylation of styrene
A. Grabulosa (2011)
10.1016/J.SUPFLU.2010.10.002
Palladocarbosilane dendrons in supercritical carbon dioxide. Catalytic behaviour in the asymmetric hydrovinylation of styrene
L. Rodriǵuez (2011)
10.1002/EJIC.201000471
Synthesis of a Chiral Palladacycle and Its Application in Asymmetric Hydrophosphanation Reactions
Y. Ding (2010)
10.1002/chem.200801505
Chirality in the absence of rigid stereogenic elements: the design of configurationally stable C3-symmetric propellers.
T. Benincori (2009)
10.1002/EJIC.200800923
Rational Design of a Novel Chiral Palladacycle: Synthesis, Optical Resolution, and Stereochemical Evaluation
Y. Ding (2009)
10.1002/ADSC.200900261
Highly Selective Cobalt-Catalyzed Hydrovinylation of Styrene
M. Grutters (2009)
10.1016/J.JORGANCHEM.2008.02.009
Palladocarbosilane dendrimers as catalysts for the asymmetric hydrovinylation of styrene in supercritical carbon dioxide
L. Rodriǵuez (2008)
10.1080/02603590701394766
ORTHO-PALLADATION OF PRIMARY AMINES: THE MYTH DISPELLED
J. Vicente (2007)
10.1016/J.JORGANCHEM.2007.02.020
Synthesis and characterization of palladium(II) complexes with chiral aminophosphine ligands: Catalytic behaviour in asymmetric hydrovinylation. Crystal structure of cis-[PdCl2(PPh((R)-NHCHCH3Ph)2)2]
R. M. Ceder (2007)
10.1016/B0-08-045047-4/00129-1
C–C Bond Formation (Part 1) by Addition Reactions: through Carbometallation Catalyzed by Group 8–11 Metals
L. Fensterbank (2007)
10.1016/J.CCR.2006.05.009
Preparation of optically pure P-stereogenic trivalent phosphorus compounds
A. Grabulosa (2007)
10.1016/B0-08-045047-4/00104-7
Palladium–Carbon π-Bonded Complexes
P. Espinet (2007)
10.1016/J.JORGANCHEM.2005.10.041
Synthesis and applications of optically active metallacycles derived from primary amines
J. Albert (2006)
10.1016/J.TETASY.2004.12.017
Palladium-catalyzed asymmetric hydrovinylation under mild conditions using monodentate chiral spiro phosphoramidite and phosphite ligands
W. Shi (2005)
10.1016/J.TETASY.2004.12.019
New principle for palladacycle resolution: diastereoselective monomer to dimer conversion
V. V. Dunina (2005)
10.1002/EJIC.200500549
Asymmetric [2+2] Cycloaddition of (E)‐2‐(Diphenylphosphanyl)styrene Promoted by a Chiral Metal Template
Wee-Chuan Yeo (2005)
10.1016/J.JORGANCHEM.2005.01.023
Resolution of β-aminophosphines with chiral cyclopalladated complexes
Jean-Michel Camus (2005)
10.1016/J.TET.2005.06.083
Asymmetric styrene dimerisation using mixed palladium–indium catalysts
R. B. Bedford (2005)
See more
Semantic Scholar Logo Some data provided by SemanticScholar