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

Unprecedented Selectivity Via Electronic Substrate Recognition In The 1,4-addition To Cyclic Olefins Using A Chiral Disulfoxide Rhodium Catalyst.

Justus J. Bürgi, Ronaldo Mariz, M. Gatti, Emma E. Drinkel, X. Luan, S. Blumentritt, A. Linden, R. Dorta
Published 2009 · Chemistry, Medicine

Cite This
Download PDF
Analyze on Scholarcy
Share
From zero to hero? Sulfoxides are generally not considered useful ligand entities in asymmetric metal catalysis. However, a chiral disulfoxide as a chelating ligand in the rhodium-catalyzed 1,4-addition of aryl boronic acids to cyclic, alpha,beta-unsaturated ketones and esters gives impressive catalytic results, thus opening the door to future applications of this new chiral ligand class.
This paper references
10.1021/OM800793Q
Chiral Dibenzazepine-Based P-Alkene Ligands and Their Rhodium Complexes: Catalytic Asymmetric 1,4 Additions to Enones
Ronaldo Mariz (2008)
10.1021/OL048240X
Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors.
Christian Defieber (2004)
10.1021/JO000462V
Synthesis of chiral bisphosphines with tunable bite angles and their applications in asymmetric hydrogenation of beta-ketoesters.
Z. Zhang (2000)
10.1021/JA0390707
Readily available [2.2.2]-bicyclooctadienes as new chiral ligands for Ir(I): catalytic, kinetic resolution of allyl carbonates.
C. Fischer (2004)
10.1021/OM9705113
Rhodium-Catalyzed Conjugate Addition of Aryl- or 1-Alkenylboronic Acids to Enones
Masaaki Sakai (1997)
10.1021/ic800354q
Synthesis, structure, and reactivity of rhodium and iridium complexes of the chelating bis-sulfoxide tBuSOC2H4SOtBu. Selective O-H activation of 2-hydroxy-isopropyl-pyridine.
T. Schaub (2008)
10.1021/OL010219Y
BINOL-based diphosphonites as ligands in the asymmetric Rh-catalyzed conjugate addition of arylboronic acids.
M. Reetz (2001)
10.1002/anie.200703612
Chiral olefins as steering ligands in asymmetric catalysis.
Christian Defieber (2008)
10.1002/HLCA.19880710427
Axially dissymmetric bis(triaryl)phosphines in the biphenyl series: synthesis of (6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine) (BIPHEMP) and analogues, and their use in Rh(I)-catalyzed asymmetric isomerizations of N,N-diethylnerylamine
R. Schmid (1988)
10.1246/CL.2008.860
Chiral Tetrafluorobenzobarrelenes as Highly Efficient Ligands for the Rhodium-catalyzed Asymmetric 1,4-Addition of Arylboronic Acids
T. Nishimura (2008)
10.1002/anie.200803230
C1-symmetric monosubstituted chiral diene ligands in asymmetric rhodium-catalyzed 1,4-addition reactions.
Thomas Gendrineau (2008)
10.1351/pac200476030465
Rhodium-catalyzed asymmetric addition of aryl- and alkenylboron reagents to electron-deficient olefins
T. Hayashi (2004)
10.1021/JA053270W
Asymmetric synthesis of 3,3-diarylpropanals with chiral diene-rhodium catalysts.
Jean-Franco̧is Paquin (2005)
10.1021/OM020241A
Stoichiometric and Catalytic Oxidation of BINAP by Dioxygen in a Rhodium(I) Complex
Kevin A. Bunten (2002)
10.1016/S0957-4166(03)00217-9
Syntheses and resolutions of new chiral biphenyl backbones: 2-amino-2′-hydroxy-6,6′-dimethyl-1,1′-biphenyl and 2-amino-2′-hydroxy-4,4′,6,6′-tetramethyl-1,1′-biphenyl
Y. Liang (2003)
10.1016/J.TET.2005.03.022
Recent advances in biaryl-type bisphosphine ligands
H. Shimizu (2005)
10.1002/ANIE.200501305
Chiral phosphine-olefin bidentate ligands in asymmetric catalysis: rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to maleimides.
R. Shintani (2005)
10.1021/JO047831Y
Preparation of C2-symmetric bicyclo[2.2.2]octa-2,5-diene ligands and their use for rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids.
Yusuke Otomaru (2005)
10.1021/CR020022Z
Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions.
T. Hayashi (2003)
10.1021/OL051533L
Catalytic asymmetric synthesis with rh-diene complexes: 1,4-addition of arylboronic acids to unsaturated esters.
Jean-Franco̧is Paquin (2005)
10.1021/ja710665q
A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins.
Ronaldo Mariz (2008)
6000; with phosphoramidites and phosphonites
S. Sakuma (2000)
10.1021/JO0207067
Rhodium-Catalyzed 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds: Large Accelerating Effects of Bases and Ligands
Ryoh Itooka (2003)
10.1002/CHEM.200701505
Highly Enantio- and s-trans C=C bond selective catalytic hydrogenation of cyclic enones: alternative synthesis of (-)-menthol.
T. Ohshima (2008)
10.1021/JO0002184
Asymmetric conjugate 1,4-addition of arylboronic acids to alpha, beta-unsaturated esters catalyzed by Rhodium(I)/(S)-binap
Sakuma (2000)
10.1021/JA012711I
Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids. Arylrhodium, oxa-pi-allylrhodium, and hydroxorhodium intermediates.
T. Hayashi (2002)
10.1021/CR020049I
New chiral phosphorus ligands for enantioselective hydrogenation.
Wenjun Tang (2003)
10.1016/S0010-8545(03)00106-1
Chiral thioether ligands: coordination chemistry and asymmetric catalysis
A. Masdeu-Bultó (2003)
10.1002/ANIE.200352453
Difluorphos, an electron-poor diphosphane: a good match between electronic and steric features.
S. Jeulin (2004)
10.1002/CHEM.200501470
Chiral phosphane alkenes (PALs): simple synthesis, applications in catalysis, and functional hemilability.
Elisabetta Piras (2006)
For an excellent recent review on the use of chiral olefin - containing ligands , see : a ) C
K. Okamoto (2005)
10.1021/OL027465+
Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands.
J. Boiteau (2003)
10.1021/JO035155E
High efficiency and enantioselectivity in the rh-catalyzed conjugate addition of arylboronic acids using monodentate phosphoramidites.
J. Boiteau (2003)
10.1002/1615-4169(20010330)343:3<264::AID-ADSC264>3.0.CO;2-T
New Chiral Diphosphine Ligands Designed to have a Narrow Dihedral Angle in the Biaryl Backbone
Takao Saito (2001)
10.1021/OL0524914
Enantiomerically pure rhodium complexes bearing 1,5-diphenyl-1,5-cyclooctadiene as a chiral diene ligand. Their use as catalysts for asymmetric 1,4-addition of phenylzinc chloride.
Asato Kina (2005)
10.1002/ANGE.200703612
Chirale Olefine als Steuerungsliganden in der asymmetrischen Katalyse
Christian Defieber (2008)
10.1016/J.TETLET.2005.08.095
Highly enantioselective rhodium-catalyzed conjugate addition of arylboronic acids to enones at room temperature
Sebastien L. X. Martina (2005)
10.1021/JA980666H
Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl- and Alkenylboronic Acids to Enones
Y. Takaya (1998)
10.1016/J.TETASY.2006.11.022
A chiral phosphepine–olefin rhodium complex as an efficient catalyst for the asymmetric conjugate addition
P. Kasák (2006)
10.1016/S0010-8545(99)00169-1
Homogeneous catalysis with transition metal complexes containing sulfur ligands
J. C. Bayón (1999)
10.1021/CR068440H
Chiral sulfur ligands for asymmetric catalysis.
M. Mellah (2007)
10.1002/1099-0690(200211)2002:21<3552::AID-EJOC3552>3.0.CO;2-4
Potassium Organotrifluoroborates in Rhodium-Catalyzed Asymmetric 1,4-Additions to Enones
Mathieu Pucheault (2002)
10.1021/CR040652W
Modified BINAP: the how and the why.
Mikaël Berthod (2005)
10.1021/JA060225V
A kinetic study on Rh/binap-catalyzed 1,4-addition of phenylboronic acid to enones: negative nonlinear effect caused by predominant homochiral dimer contribution.
Asato Kina (2006)
10.1021/JA037367Z
A chiral chelating diene as a new type of chiral ligand for transition metal catalysts: its preparation and use for the rhodium-catalyzed asymmetric 1,4-addition.
T. Hayashi (2003)
10.1021/JA044021V
Catalytic asymmetric arylative cyclization of alkynals: phosphine-free rhodium/diene complexes as efficient catalysts.
R. Shintani (2005)
10.1021/JA044790E
C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands: their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines.
N. Tokunaga (2004)
For recent reviews on sulfide and sulfoxide ligands in catalysis , see : a ) J . C . Bayon , C . Claver , A . M . Masdeu - Bulto
A. M. Masdeu-Bulto (1999)
10.1021/JA0671013
Chiral phosphine-olefin ligands in the rhodium-catalyzed asymmetric 1,4-addition reactions.
W. Duan (2007)
10.1021/OL052756E
High Performance of a Chiral Diene−Rhodium Catalyst for the Asymmetric 1,4-Addition of Arylboroxines to α,β-Unsaturated Ketones
F. Chen (2006)
10.1016/J.JORGANCHEM.2006.04.042
Enantioselective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds catalyzed by rhodium(I)-chiral phosphoramidite complexes
K. Kurihara (2007)



This paper is referenced by
10.1002/anie.201102586
Chiral sulfoxide-olefin ligands: completely switchable stereoselectivity in rhodium-catalyzed asymmetric conjugate additions.
G. Chen (2011)
10.1021/ol3015896
Efficient pseudo-enantiomeric carbohydrate olefin ligands.
Holger Grugel (2012)
10.1021/ACS.JCHEMED.6B00102
The Two Faces of Sulfinates: Illustrating Umpolung Reactivity
Adabelia Tapia-Pineda (2016)
10.1016/J.TET.2015.01.054
The first application of C2-symmetric chiral sulfurous diamide as efficient sulfur–olefin hybrid ligands for Rh-catalyzed asymmetric 1,4-addition reactions
Q. Chen (2016)
10.1039/b908043k
Enantiopure sulfoxides: recent applications in asymmetric synthesis.
M. Carreño (2009)
10.1016/J.TETASY.2011.02.020
Indole-olefin-oxazoline (IndOlefOx)-ligands: synthesis and utilization in asymmetric Rh-catalyzed conjugate addition
Noora Kuuloja (2011)
10.1002/anie.201915470
Enantioselective Construction of Axially Chiral Amino Sulfide Vinyl Arenes via Chiral Sulfide-Catalyzed Electrophilic Carbothiolation of Alkynes.
Xiaodan Zhao (2020)
10.1016/J.TET.2011.02.023
Synthesis of C3- and C2-symmetric tris- and bis-sulfoxide ligands by asymmetric oxidation
P. K. Dornan (2011)
10.1021/CS200562N
Rhodium-Catalyzed Asymmetric Arylation
P. Tian (2012)
10.1002/EJIC.201500331
Synthesis of BINAM‐Based Chiral Di‐1,2,3‐triazolylidene Complexes and Application of the Di‐NHC RhI Catalyst in Enantioselective Hydrosilylation
S. N. Sluijter (2015)
10.1002/chem.201001938
Comparing the enantioselective power of steric and electrostatic effects in transition-metal-catalyzed asymmetric synthesis.
A. Poater (2010)
10.1021/jo400700m
Flexible C2-symmetric bis-sulfoxides as ligands in enantioselective 1,4-addition of boronic acids to electron-deficient alkenes.
N. Khiar (2013)
10.1002/EJIC.200900521
PNSO Ligands as a Tool to Study Metal Bonding of Electron‐Deficient Sulfinyl Groups
Marc Reves (2009)
10.1016/J.TETLET.2010.12.044
Rhodium-catalyzed asymmetric addition of arylboronic acids to γ-phthalimido-substituted-α,β-unsaturated carboxylic acid esters: an approach to γ-amino acids
Fuzhong Han (2011)
10.1021/ja207748r
Chiral allene-containing phosphines in asymmetric catalysis.
F. Cai (2011)
10.1021/jacs.5b07034
Rhodium-Catalyzed Asymmetric 1,4-Addition of α,β-Unsaturated Imino Esters Using Chiral Bicyclic Bridgehead Phosphoramidite Ligands.
Ansoo Lee (2015)
10.1002/chir.22159
Asymmetric allylation of α-ketoester-derived N-benzoylhydrazones promoted by chiral sulfoxides/N-oxides Lewis bases: highly enantioselective synthesis of quaternary α-substituted α-allyl-α-amino acids.
Gloria Reyes-Rangel (2013)
10.1002/ADSC.200900792
tert‐Butanesulfinylphosphines: Simple Chiral Ligands in Rhodium‐Catalyzed Asymmetric Addition of Arylboronic Acids to Electron‐Deficient Olefins
Feng Lang (2010)
10.1002/ANGE.201411073
Chirale Sulfoxidliganden für die asymmetrische Katalyse
B. Trost (2015)
10.1016/J.TET.2012.02.038
Chiral sulfoxide–olefin ligands: tunable stereoselectivity in Rh-catalyzed asymmetric 1,4-additions
Gui-hua Chen (2012)
10.3390/molecules18010014
An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Ketones
Y. Yamamoto (2012)
10.1039/c6ob02651f
Cooperativity of axial and centre chirality in the biaryl disulfoxide/Rh(i)-catalysed asymmetric 1,4-addition of arylboronic aids to 2-cyclohexenone: a DFT study.
Gao-Feng Zha (2017)
10.1021/ol201151r
Design of chiral sulfoxide-olefins as a new class of sulfur-based olefin ligands for asymmetric catalysis.
Wei-Yi Qi (2011)
10.1016/B978-0-08-095167-6.00510-3
5.8 Asymmetric S–O Bond Formation by Oxidation
H. Ishitani (2012)
10.1039/c3cc42673d
Application of chiral N-tert-butylsulfinyl vinyl aziridines in Rh(I) catalyzed 1,4-addition of aryl boronic acids to cyclic enones.
Q. Chen (2013)
10.1016/B978-0-08-097742-3.00406-7
4.04 Metal-Catalyzed Asymmetric Nucleophilic Addition to Electron-Deficient Alkenes
M. Mauduit (2014)
10.1021/jo2011472
A class of benzene backbone-based olefin-sulfoxide ligands for Rh-catalyzed enantioselective addition of arylboronic acids to enones.
F. Xue (2011)
10.1021/ol200841x
Sulfoxide-alkene hybrids: a new class of chiral ligands for the Hayashi-Miyaura reaction.
Tobias Thaler (2011)
10.1016/J.TETASY.2016.05.004
Rh-catalyzed asymmetric 1,4-addition reactions to α,β-unsaturated carbonyl and related compounds: an update
M. Heravi (2016)
10.1002/chem.201001749
C2-symmetric chiral disulfoxide ligands in rhodium-catalyzed 1,4-addition: from ligand synthesis to the enantioselection pathway.
Ronaldo Mariz (2010)
10.1021/OM4000067
Synthesis, Structure, and Catalytic Studies of Palladium and Platinum Bis-Sulfoxide Complexes
Emma E. Drinkel (2014)
10.1002/EJOC.201402109
Rhodium(I)‐Catalyzed [2+2+2+2] Cycloaddition of Diynes To Form Cyclooctatetraenes
Daniel J Nasrallah (2014)
See more
Semantic Scholar Logo Some data provided by SemanticScholar