Asymmetric transfer hydrogenation of 3-nitroquinolines: facile access to cyclic nitro compounds with two contiguous stereocenters.

Hi, neighbor! The first organocatalyzed asymmetric transfer hydrogenation of aromatic nitro compounds was successfully developed with up to 99 % ee. The new methodology provides a direct and facile access to enantiopure cyclic nitro compounds with two contiguous stereocenters.

[1]  蔡先锋,et al.  Asymmetric Transfer Hydrogenation of 3-Nitroquinolines:Facile Access to Cyclic Nitro Compounds with Two Contiguous Stereocenters , 2013 .

[2]  Yong‐Gui Zhou,et al.  Enantioselective iridium-catalyzed hydrogenation of 1- and 3-substituted isoquinolinium salts. , 2013, Angewandte Chemie.

[3]  K. Mashima,et al.  Asymmetric hydrogenation of isoquinolinium salts catalyzed by chiral iridium complexes: direct synthesis for optically active 1,2,3,4-tetrahydroisoquinolines. , 2013, Angewandte Chemie.

[4]  I. Pápai,et al.  Dihydrooxazine oxides as key intermediates in organocatalytic Michael additions of aldehydes to nitroalkenes. , 2012, Angewandte Chemie.

[5]  L. Gong,et al.  Highly enantioselective transfer hydrogenation of quinolines catalyzed by gold phosphates: achiral ligand tuning and chiral-anion control of stereoselectivity. , 2012, Angewandte Chemie.

[6]  F. Glorius,et al.  Asymmetric hydrogenation of thiophenes and benzothiophenes. , 2012, Journal of the American Chemical Society.

[7]  W. Kreis,et al.  Nicotinamide‐Dependent Ene Reductases as Alternative Biocatalysts for the Reduction of Activated Alkenes , 2012 .

[8]  Xumu Zhang,et al.  Highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes. , 2012, Angewandte Chemie.

[9]  Yong‐Gui Zhou,et al.  Enantioselective iridium-catalyzed hydrogenation of 3,4-disubstituted isoquinolines. , 2012, Angewandte Chemie.

[10]  Yan Yan,et al.  Highly enantioselective reduction of β-amino nitroolefins with a simple N-sulfinyl urea as bifunctional catalyst. , 2012, Chemistry.

[11]  A. Maguire,et al.  Biocatalytic Approaches to the Henry (Nitroaldol) Reaction , 2012 .

[12]  R. Kuwano,et al.  Catalytic asymmetric hydrogenation of naphthalenes. , 2012, Angewandte Chemie.

[13]  Yong‐Gui Zhou,et al.  Asymmetric hydrogenation of heteroarenes and arenes. , 2012, Chemical reviews.

[14]  S. You,et al.  Transfer hydrogenation with Hantzsch esters and related organic hydride donors. , 2012, Chemical Society reviews.

[15]  F. Glorius,et al.  Ruthenium-NHC-katalysierte hoch asymmetrische Hydrierung von Benzofuranen† , 2012 .

[16]  F. Glorius,et al.  Ruthenium NHC catalyzed highly asymmetric hydrogenation of benzofurans. , 2012, Angewandte Chemie.

[17]  Yong‐Gui Zhou,et al.  Dihydrophenanthridine: a new and easily regenerable NAD(P)H model for biomimetic asymmetric hydrogenation. , 2012, Journal of the American Chemical Society.

[18]  M. Rueping,et al.  Direct enantioselective access to 4-substituted tetrahydroquinolines by catalytic asymmetric transfer hydrogenation of quinolines. , 2011, Organic & biomolecular chemistry.

[19]  A. Chan,et al.  Highly enantioselective hydrogenation of quinolines using phosphine-free chiral cationic ruthenium catalysts: scope, mechanism, and origin of enantioselectivity. , 2011, Journal of the American Chemical Society.

[20]  J. Paradies,et al.  Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins. , 2011, Organic & biomolecular chemistry.

[21]  Yong‐Gui Zhou,et al.  Highly enantioselective partial hydrogenation of simple pyrroles: a facile access to chiral 1-pyrrolines. , 2011, Journal of the American Chemical Society.

[22]  M. Rueping,et al.  Advances in catalytic metal-free reductions: from bio-inspired concepts to applications in the organocatalytic synthesis of pharmaceuticals and natural products , 2011 .

[23]  R. Kuwano,et al.  Catalytic asymmetric hydrogenation of N-Boc-imidazoles and oxazoles. , 2011, Journal of the American Chemical Society.

[24]  K. Zangger,et al.  Reductive biotransformation of nitroalkenes via nitroso-intermediates to oxazetes catalyzed by xenobiotic reductase A (XenA). , 2011, Organic & biomolecular chemistry.

[25]  F. Glorius,et al.  Ligandengesteuerte hoch regioselektive und asymmetrische Hydrierung von Chinoxalinen, katalysiert durch Ruthenium‐Komplexe von N‐heterocyclischen Carbenen , 2011 .

[26]  F. Glorius,et al.  Ligand-controlled highly regioselective and asymmetric hydrogenation of quinoxalines catalyzed by ruthenium N-heterocyclic carbene complexes. , 2011, Angewandte Chemie.

[27]  Yong‐Gui Zhou,et al.  Convergent asymmetric disproportionation reactions: metal/Brønsted acid relay catalysis for enantioselective reduction of quinoxalines. , 2011, Journal of the American Chemical Society.

[28]  Shou‐Fei Zhu,et al.  Transition metal-catalyzed enantioselective hydrogenation of enamines and imines. , 2011, Chemical reviews.

[29]  M. Rueping,et al.  Brønsted acid differentiated metal catalysis by kinetic discrimination. , 2011, Chemical communications.

[30]  J. Benet‐Buchholz,et al.  Asymmetric Hydrogenation of Heteroaromatic Compounds Mediated by Iridium-(P-OP) Complexes , 2010 .

[31]  Xumu Zhang,et al.  Iridium‐Catalyzed Asymmetric Hydrogenation of Quinoline Derivatives with C3*‐TunePhos , 2010 .

[32]  M. Rueping,et al.  Asymmetric Brønsted acid catalysis in aqueous solution , 2010 .

[33]  M. Rueping,et al.  Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation , 2010 .

[34]  G. Lin,et al.  Rhodium-catalyzed asymmetric conjugate addition of organoboronic acids to nitroalkenes using chiral bicyclo[3.3.0] diene ligands. , 2010, Angewandte Chemie.

[35]  Yong‐Gui Zhou,et al.  Pd-catalyzed asymmetric hydrogenation of unprotected indoles activated by Brønsted acids. , 2010, Journal of the American Chemical Society.

[36]  M. Rueping,et al.  Thieme Chemistry Journal Awardees - Where Are They Now? Asymmetric Brønsted Acid Catalyzed Transfer Hydrogenations , 2010 .

[37]  M. Rueping,et al.  The first general, efficient and highly enantioselective reduction of quinoxalines and quinoxalinones. , 2010, Chemistry.

[38]  A. Chan,et al.  Asymmetric hydrogenation of quinoxalines with diphosphinite ligands: a practical synthesis of enantioenriched, substituted tetrahydroquinoxalines. , 2009, Angewandte Chemie.

[39]  E. Carreira,et al.  Transfer hydrogenation in water: enantioselective, catalytic reduction of (E)-beta,beta-disubstituted nitroalkenes. , 2009, Organic letters.

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

[41]  Raquel P. Herrera,et al.  Catalytic Enantioselective Aza-Henry Reactions , 2009 .

[42]  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.

[43]  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.

[44]  J. Bats,et al.  Asymmetric Counterion Pair Catalysis: An Enantioselective Brønsted Acid‐Catalyzed Protonation , 2008 .

[45]  K. Fisher,et al.  Highly enantioselective reduction of beta,beta-disubstituted aromatic nitroalkenes catalyzed by Clostridium sporogenes. , 2008, The Journal of organic chemistry.

[46]  Shufen Xu,et al.  Brønsted Acid Catalyzed Asymmetric Reduction of 2- and 2,9-Substituted 1,10-Phenanthrolines , 2008 .

[47]  H. Pellissier.  Recent Developments in Dynamic Kinetic Resolution , 2008 .

[48]  R. Kuwano,et al.  Catalytic asymmetric hydrogenation of 2,3,5-trisubstituted pyrroles. , 2008, Journal of the American Chemical Society.

[49]  D. MacMillan,et al.  Enantioselective organocatalytic transfer hydrogenation reactions using Hantzsch esters. , 2007, Accounts of chemical research.

[50]  S. Connon.  Asymmetric organocatalytic reductions mediated by dihydropyridines. , 2007, Organic & biomolecular chemistry.

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

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

[53]  B. List,et al.  Organocatalytic asymmetric transfer hydrogenation of nitroolefins. , 2007, Journal of the American Chemical Society.

[54]  Magnus Rueping,et al.  Organokatalytische enantioselektive Reduktion von Pyridinen , 2007 .

[55]  M. Rueping,et al.  Organocatalytic enantioselective reduction of pyridines. , 2007, Angewandte Chemie.

[56]  C. Palomo,et al.  Recent Advances in the Catalytic Asymmetric Nitroaldol (Henry) Reaction , 2007 .

[57]  P. Macheroux,et al.  Asymmetric bioreduction of activated alkenes using cloned 12-oxophytodienoate reductase isoenzymes OPR-1 and OPR-3 from Lycopersicon esculentum (tomato): a striking change of stereoselectivity. , 2007, Angewandte Chemie.

[58]  A. Pfaltz,et al.  Iridium catalysts with bicyclic pyridine-phosphinite ligands: asymmetric hydrogenation of olefins and furan derivatives. , 2006, Angewandte Chemie.

[59]  Magnus Rueping,et al.  Eine hoch enantioselektive Brønsted‐Säure‐katalysierte Kaskadenreaktion: organokatalytische Transferhydrierung von Chinolinen und deren Anwendung in der Synthese von Alkaloiden , 2006 .

[60]  M. Rueping,et al.  A highly enantioselective Brønsted acid catalyzed cascade reaction: organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids. , 2006, Angewandte Chemie.

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

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

[63]  J. Xia,et al.  One-Pot Synthesis and Aromatization of 1,4-Dihydropyridines in Refluxing Water , 2005 .

[64]  A. Hoveyda,et al.  Enantioselective synthesis of nitroalkanes bearing all-carbon quaternary stereogenic centers through Cu-catalyzed asymmetric conjugate additions. , 2005, Journal of the American Chemical Society.

[65]  E. Carreira,et al.  Convenient catalytic, enantioselective conjugate reduction of nitroalkenes using CuF2. , 2004, Organic letters.

[66]  L. Tang,et al.  Highly enantioselective conjugate addition of malonate and beta-ketoester to nitroalkenes: asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids. , 2004, Journal of the American Chemical Society.

[67]  M. Yan,et al.  An investigation of the reaction of 2-aminobenzaldehyde derivatives with conjugated nitro-olefins: an easy and efficient synthesis of 3-nitro-1,2-dihydroquinolines and 3-nitroquinolines. , 2004, The Journal of organic chemistry.

[68]  J. Genêt.  Asymmetric catalytic hydrogenation. Design of new Ru catalysts and chiral ligands: from laboratory to industrial applications. , 2003, Accounts of chemical research.

[69]  E. Carreira,et al.  Catalytic Enantioselective Conjugate Reduction of β,β‐Disubstituted Nitroalkenes , 2003 .

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

[71]  A. Hoveyda,et al.  Cu-catalyzed enantioselective conjugate addition of alkylzincs to cyclic nitroalkenes: catalytic asymmetric synthesis of cyclic alpha-substituted ketones. , 2002, Journal of the American Chemical Society.

[72]  D. Enders,et al.  Asymmetric Michael Additions to Nitroalkenes , 2002 .

[73]  R. Kuwano,et al.  Catalytic asymmetric hydrogenation of heteroaromatic compounds, indoles [12] , 2000 .

[74]  H. Ohta,et al.  Asymmetric reduction of nitro olefins by fermenting bakers' yeast , 1989 .