Phosphine-free chiral metal catalysts for highly effective asymmetric catalytic hydrogenation.

In addition to the brilliant chiral phosphorus metal catalysts, chiral phosphine-free metal complexes find increasing application as catalysts for asymmetric hydrogenation. In this account, two types of chiral phosphine-free ligands, N-heterocyclic carbene-based C,N-ligands and diamine-based N,N-ligands, in the homogeneous asymmetric hydrogenation of prochiral ketones, imines and quinolines are reviewed.

[1]  J. Lacour,et al.  Chiral anion-mediated asymmetric ion pairing chemistry. , 2009, Chemical communications.

[2]  X. Wu,et al.  pH-Regulated Asymmetric Transfer Hydrogenation of Quinolinesin Water , 2009 .

[3]  V. Ratovelomanana-Vidal,et al.  Unprecedented halide dependence on catalytic asymmetric hydrogenation of 2-aryl- and 2-alkyl-substituted quinolinium salts by using Ir complexes with difluorphos and halide ligands. , 2009, Chemistry.

[4]  K. Burgess,et al.  Synthesis of vicinal dimethyl chirons by asymmetric hydrogenation of trisubstituted alkenes. , 2009, Journal of the American Chemical Society.

[5]  Jianliang Xiao,et al.  pH-regulated asymmetric transfer hydrogenation of quinolines in water. , 2009, Angewandte Chemie.

[6]  M. Wills,et al.  Ir(III) complexes of diamine ligands for asymmetric ketone hydrogenation , 2009 .

[7]  S. Nolan,et al.  N-heterocyclic carbenes in late transition metal catalysis. , 2009, Chemical reviews.

[8]  Zheng Wang,et al.  Spiro[4,4]-1,6-nonadiene-based phosphine-oxazoline ligands for iridium-catalyzed enantioselective hydrogenation of ketimines. , 2009, Angewandte Chemie.

[9]  B. Feringa,et al.  Iridium/monodentate phosphoramidite catalyzed asymmetric hydrogenation of N-aryl imines. , 2009, Journal of the American Chemical Society.

[10]  Yanmei He,et al.  Highly enantioselective hydrogenation of quinolines under solvent-free or highly concentrated conditions , 2009 .

[11]  Jianliang Xiao,et al.  Metal-Brønsted acid cooperative catalysis for asymmetric reductive amination. , 2009, Journal of the American Chemical Society.

[12]  K. Burgess,et al.  Aldol-type chirons from asymmetric hydrogenations of trisubstituted alkenes. , 2009, Organic letters.

[13]  Shubin Liu,et al.  Mechanism and Influence of Acid in Hydrogenation of Ketones by η6-Arene/N-Tosylethylenediamine Ruthenium(II) , 2009 .

[14]  Yong‐Gui Zhou,et al.  Highly enantioselective iridium-catalyzed hydrogenation of 2-benzylquinolines and 2-functionalized and 2,3-disubstituted quinolines. , 2009, The Journal of organic chemistry.

[15]  M. Wills,et al.  Asymmetric hydrogenation of ketones using Ir(III) complexes of N-alkyl-N'-tosyl-1,2-ethanediamine ligands , 2009 .

[16]  T. Ikariya,et al.  Remarkable Positive Effect of Silver Salts on Asymmetric Hydrogenation of Acyclic Imines with Cp*Ir Complexes Bearing Chiral N-Sulfonylated Diamine Ligands , 2009 .

[17]  Pan‐Lin Shao,et al.  [4+2] cycloaddition of ketenes with N-benzoyldiazenes catalyzed by N-heterocyclic carbenes. , 2009, Angewandte Chemie.

[18]  R. Kuwano.  CATALYTIC ASYMMETRIC HYDROGENATION OF 5-MEMBERED HETEROAROMATICS , 2008 .

[19]  H. Seo,et al.  Recent Developments of Chiral Diaminocarbene-Metal Complexes for Asymmetric Catalysis , 2008 .

[20]  Lijin Xu,et al.  Air-stable and phosphine-free iridium catalysts for highly enantioselective hydrogenation of quinoline derivatives. , 2008, Organic letters.

[21]  Masato M. Ito,et al.  Well-Defined Triflylamide-Tethered Arene−Ru(Tsdpen) Complexes for Catalytic Asymmetric Hydrogenation of Ketones , 2008 .

[22]  A. Chan,et al.  Hydrogenation of quinolines using a recyclable phosphine-free chiral cationic ruthenium catalyst: enhancement of catalyst stability and selectivity in an ionic liquid. , 2008, Angewandte Chemie.

[23]  Jianliang Xiao,et al.  Chiral counteranion-aided asymmetric hydrogenation of acyclic imines. , 2008, Journal of the American Chemical Society.

[24]  Jianliang Xiao,et al.  Asymmetric hydrogenation of cyclic imines with an ionic Cp*Rh(III) catalyst. , 2008, Journal of the American Chemical Society.

[25]  P. Andersson,et al.  Phosphine-free Cp*Ru(diamine) catalysts in the hydrogenation of imines. , 2008, Chemistry, an Asian journal.

[26]  K. Burgess,et al.  Asymmetric hydrogenation approaches to valuable, acyclic 1,3-hydroxymethyl chirons. , 2008, Journal of the American Chemical Society.

[27]  K. Burgess,et al.  Iridium‐Catalyzed Asymmetric Hydrogenation of Vinyl Ethers , 2008 .

[28]  B. Feringa,et al.  Asymmetric hydrogenation of quinolines catalyzed by iridium complexes of monodentate BINOL-derived phosphoramidites , 2008 .

[29]  T. Ikariya,et al.  Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts. , 2007, Accounts of chemical research.

[30]  T. Rauchfuss,et al.  Homogeneous catalytic reduction of dioxygen using transfer hydrogenation catalysts. , 2007, Journal of the American Chemical Society.

[31]  D. Enders,et al.  Organocatalysis by N-heterocyclic carbenes. , 2007, Chemical reviews.

[32]  Yong‐Gui Zhou.  Asymmetric hydrogenation of heteroaromatic compounds. , 2007, Accounts of chemical research.

[33]  K. Burgess,et al.  Asymmetric hydrogenation routes to deoxypolyketide chirons. , 2007, Chemistry.

[34]  S. You.  Recent developments in asymmetric transfer hydrogenation with Hantzsch esters: a biomimetic approach. , 2007, Chemistry, an Asian journal.

[35]  Jianliang Xiao,et al.  Aqueous-phase asymmetric transfer hydrogenation of ketones--a greener approach to chiral alcohols. , 2007, Chemical communications.

[36]  M. Reetz,et al.  Mixtures of chiral phosphorous acid diesters and achiral p ligands in the enantio- and diastereoselective hydrogenation of ketimines. , 2007, Angewandte Chemie.

[37]  T. Ohkuma,et al.  Asymmetric hydrogenation of alpha-hydroxy ketones catalyzed by MsDPEN-Cp*Ir(III) complex. , 2007, Organic letters.

[38]  Nicolas Marion,et al.  N-heterocyclic carbenes as organocatalysts. , 2007, Angewandte Chemie.

[39]  K. Burgess,et al.  Synthesis of (S,R,R,S,R,S)-4,6,8,10,16,18- hexamethyldocosane from Antitrogus parvulus via diastereoselective hydrogenations. , 2007, Organic letters.

[40]  S. Bellemin‐Laponnaz,et al.  Mixed oxazoline-carbenes as stereodirecting ligands for asymmetric catalysis , 2007 .

[41]  P. Andersson,et al.  New ligands for the RuCp∗-diamine catalysed asymmetric hydrogenation of aryl ketones , 2007 .

[42]  Y. Li,et al.  Enantioselective hydrogenation of quinolines catalyzed by Ir(BINAP)-cored dendrimers: dramatic enhancement of catalytic activity. , 2007, Organic letters.

[43]  K. Burgess,et al.  Alpha,omega-functionalized 2,4-dimethylpentane dyads and 2,4,6-trimethylheptane triads through asymmetric hydrogenation. , 2007, Angewandte Chemie.

[44]  A. Chan,et al.  Asymmetric hydrogenation of quinolines with high substrate/catalyst ratio. , 2007, Chemical communications.

[45]  R. Noyori,et al.  Asymmetric Hydrogenation of α-Chloro Aromatic Ketones Catalyzed by η6-Arene/TsDPEN−Ruthenium(II) Complexes , 2007 .

[46]  E. Herdtweck,et al.  Chiral N-Heterocyclic Carbenes with Restricted Flexibility in Asymmetric Catalysis† , 2007 .

[47]  P. Andersson,et al.  Asymmetric hydrogenation of tri-substituted alkenes with Ir-NHC-thiazole complexes , 2006 .

[48]  Shou‐Fei Zhu,et al.  Well-defined chiral spiro iridium/phosphine-oxazoline cationic complexes for highly enantioselective hydrogenation of imines at ambient pressure. , 2006, Journal of the American Chemical Society.

[49]  R. Noyori,et al.  Mechanism of asymmetric hydrogenation of acetophenone catalyzed by chiral eta(6)-arene-N-tosylethylenediamine-ruthenium(II) complexes. , 2006, Chemistry, an Asian journal.

[50]  M. Yoshimura,et al.  Enantioselective hydrogenation of aromatic ketones catalyzed by Ru complexes of Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R'-Py. , 2006, Journal of the American Chemical Society.

[51]  R. Noyori,et al.  The hydrogenation/transfer hydrogenation network: asymmetric hydrogenation of ketones with chiral eta6-arene/N-Tosylethylenediamine-ruthenium(II) catalysts. , 2006, Journal of the American Chemical Society.

[52]  A. Pfaltz,et al.  Synthesis and application of chiral N-heterocyclic carbene-oxazoline ligands: iridium-catalyzed enantioselective hydrogenation. , 2006, Chemistry.

[53]  M. Reetz,et al.  Asymmetric hydrogenation of quinolines catalyzed by iridium complexes of BINOL-derived diphosphonites. , 2006, Chemical communications.

[54]  E. Herdtweck,et al.  Chiral N-Heterocyclic Carbene Ligands Derived from 2,2‘-Bipiperidine and Partially Reduced Biisoquinoline: Rhodium and Iridium Complexes in Asymmetric Catalysis† , 2006 .

[55]  Xiuwen Han,et al.  Asymmetric hydrogenation of quinolines and isoquinolines activated by chloroformates. , 2006, Angewandte Chemie.

[56]  P. Andersson,et al.  Mechanistic aspects of transition metal-catalyzed hydrogen transfer reactions. , 2006, Chemical Society reviews.

[57]  Elisabetta Alberico,et al.  Asymmetric transfer hydrogenation: chiral ligands and applications. , 2006, Chemical Society reviews.

[58]  K. Burgess,et al.  Mechanistic insights into iridium-catalyzed asymmetric hydrogenation of dienes. , 2005, Chemistry.

[59]  F. Glorius.  Asymmetric hydrogenation of aromatic compounds. , 2005, Organic & biomolecular chemistry.

[60]  P. Andersson,et al.  Mechanistic insights into the phosphine-free RuCp*-diamine-catalyzed hydrogenation of aryl ketones: experimental and theoretical evidence for an alcohol-mediated dihydrogen activation. , 2005, Journal of the American Chemical Society.

[61]  K. Burgess,et al.  Catalytic homogeneous asymmetric hydrogenations of largely unfunctionalized alkenes. , 2005, Chemical reviews.

[62]  A. Chan,et al.  Air-stable Ir-(P-Phos) complex for highly enantioselective hydrogenation of quinolines and their immobilization in poly(ethylene glycol) dimethyl ether (DMPEG). , 2005, Chemical communications.

[63]  K. Burgess,et al.  Stereoselective hydrogenations of aryl-substituted dienes. , 2005, Chemical communications.

[64]  S. Bellemin‐Laponnaz,et al.  Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis. , 2004, Chemical Society reviews.

[65]  K. Burgess,et al.  Electronic effects steer the mechanism of asymmetric hydrogenations of unfunctionalized aryl-substituted alkenes. , 2004, Journal of the American Chemical Society.

[66]  R Morris Bullock,et al.  Catalytic ionic hydrogenations. , 2004, Chemistry.

[67]  D. Enders,et al.  Nucleophilic carbenes in asymmetric organocatalysis. , 2004, Accounts of chemical research.

[68]  K. Burgess,et al.  Iridium-mediated asymmetric hydrogenation of 2,3-diphenylbutadiene: a revealing kinetic study. , 2003, Journal of the American Chemical Society.

[69]  Xiuwen Han,et al.  Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines. , 2003, Journal of the American Chemical Society.

[70]  C. Bolm,et al.  Synthesis of iridium complexes with novel planar chiral chelating imidazolylidene ligands , 2003 .

[71]  Xumu Zhang,et al.  New chiral phosphorus ligands for enantioselective hydrogenation. , 2003, Chemical reviews.

[72]  K. Burgess,et al.  Chiral N-heterocyclic carbene-transition metal complexes in asymmetric catalysis , 2003 .

[73]  M. T. Powell,et al.  Optically active iridium imidazol-2-ylidene-oxazoline complexes: preparation and use in asymmetric hydrogenation of arylalkenes. , 2003, Journal of the American Chemical Society.

[74]  B. Pugin,et al.  Selective Hydrogenation for Fine Chemicals: Recent Trends and New Developments , 2003 .

[75]  P. Janvier,et al.  Synthesis of a new water-soluble C(2)-symmetric chiral diamine: preliminary investigation of its catalytic properties for asymmetric hydrogenation under biphasic conditions. , 2002, The Journal of organic chemistry.

[76]  A. Ferrand,et al.  Hydrophilic diamine ligands for catalytic asymmetric hydrogenation of CO bonds , 2002 .

[77]  W. Herrmann.  N-heterocyclic carbenes: a new concept in organometallic catalysis. , 2002, Angewandte Chemie.

[78]  A. Baiker,et al.  Asymmetric Hydrogenation of Activated Ketones on Platinum: Relevant and Spectator Species , 2002 .

[79]  Xumu Zhang,et al.  Highly Enantioselective Hydrogenation of Acyclic Imines Catalyzed by Ir–f‐Binaphane Complexes , 2001 .

[80]  M. T. Powell,et al.  Chiral imidazolylidine ligands for asymmetric hydrogenation of aryl alkenes. , 2001, Journal of the American Chemical Society.

[81]  Masato M. Ito,et al.  Hydrogenation of aromatic ketones catalyzed by (η5-C5(CH3)5)Ru complexes bearing primary amines , 2001 .

[82]  Ryoji Noyori,et al.  Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of Ketones. , 2001, Angewandte Chemie.

[83]  T. Osawa,et al.  Progress of enantio-differentiating hydrogenation of prochiral ketones over asymmetrically modified nickel catalysts and a newly proposed enantio-differentiation model , 2000 .

[84]  M. Lemaire,et al.  Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis. , 2000, Chemical reviews.

[85]  A. Pfaltz,et al.  PhosphinooxazolinesA New Class of Versatile, Modular P,N-Ligands for Asymmetric Catalysis , 2000 .

[86]  Ryoji Noyori,et al.  The Metal−Ligand Bifunctional Catalysis: A Theoretical Study on the Ruthenium(II)-Catalyzed Hydrogen Transfer between Alcohols and Carbonyl Compounds , 2000 .

[87]  S. Buchwald,et al.  Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Olefins with a Cationic Zirconocene Catalyst , 1999 .

[88]  F. Touchard,et al.  Cationic complexes with chiral diamine or dithiourea ligands as catalysts for molecular asymmetric hydrogenation , 1999 .

[89]  A. Pfaltz,et al.  Enantioselective Hydrogenation of Olefins with Iridium-Phosphanodihydrooxazole Catalysts. , 1998, Angewandte Chemie.

[90]  W. Herrmann,et al.  CHIRAL OXAZOLINE/IMIDAZOLINE-2-YLIDENE COMPLEXES , 1998 .

[91]  S. Hanessian,et al.  trans-1,2-Diaminocyclohexane Derivatives as Chiral Reagents, Scaffolds, and Ligands for Catalysis: Applications in Asymmetric Synthesis and Molecular Recognition. , 1997, Chemical reviews.

[92]  C. Pinel,et al.  Chiral nitrogen-metal complexes for the asymmetric reduction of ketones , 1997 .

[93]  and Ryoji Noyori,et al.  Asymmetric Transfer Hydrogenation Catalyzed by Chiral Ruthenium Complexes , 1997 .

[94]  W. Herrmann,et al.  Chiral Heterocylic Carbenes in Asymmetric Homogeneous Catalysis , 1996 .

[95]  T. Ikariya,et al.  Asymmetric Transfer Hydrogenation of Imines , 1996 .

[96]  R. Noyori,et al.  Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using a Formic Acid−Triethylamine Mixture , 1996 .

[97]  T. Ikariya,et al.  Preferential hydrogenation of aldehydes and ketones. , 1995 .

[98]  T. Ikariya,et al.  Asymmetric Transfer Hydrogenation of Aromatic Ketones Catalyzed by Chiral Ruthenium(II) Complexes , 1995 .

[99]  T. Ikariya,et al.  PRACTICAL ENANTIOSELECTIVE HYDROGENATION OF AROMATIC KETONES , 1995 .

[100]  S. Buchwald,et al.  CATALYTIC ASYMMETRIC HYDROGENATION OF IMINES WITH A CHIRAL TITANOCENE CATALYST : SCOPE AND LIMITATIONS , 1994 .

[101]  A. Togni,et al.  Nitrogen donors in organometallic chemistry and homogeneous catalysis , 1994 .

[102]  S. Buchwald,et al.  Asymmetric hydrogenation of unfunctionalized trisubstituted olefins with a chiral titanocene catalyst , 1993 .

[103]  Richard L. Harlow,et al.  A stable crystalline carbene , 1991 .

[104]  R. Crabtree.  Iridium compounds in catalysis , 1979 .

[105]  G. E. Morris,et al.  CATIONIC IRIDIUM DIOLEFIN COMPLEXES AS ALKENE HYDROGENATION CATALYSTS AND THE ISOLATION OF SOME RELATED HYDRIDO COMPLEXES , 1978 .

[106]  H. Kricheldorf,et al.  A New Synthesis of Isocyanates and Isothiocyanates , 1968 .