Asymmetric hydroamination catalyzed by a new chiral zirconium system: reaction scope and mechanism.

A new class of chiral zirconium complexes supported by chiral tridentate [O(-)NO(-)]-type of ligands derived from amino acids were synthesized and structurally characterized. They catalyzed asymmetric hydroamination/cyclization of primary aminoalkenes to give five- and six-membered N-heterocyclic amines with up to 94% ee.

[1]  T. Windus,et al.  Highly enantioselective zirconium-catalyzed cyclization of aminoalkenes. , 2013, Journal of the American Chemical Society.

[2]  J. Ke,et al.  Synergistic catalysis in the Sonogashira coupling reaction: quantitative kinetic investigation of transmetalation. , 2013, Angewandte Chemie.

[3]  S. Chemler,et al.  Chiral Indoline Synthesis Via Enantioselective Intramolecular Copper-Catalyzed Alkene Hydroamination. , 2012, Organometallics.

[4]  T. Emge,et al.  A chiral phenoxyamine magnesium catalyst for the enantioselective hydroamination/cyclization of aminoalkenes and intermolecular hydroamination of vinyl arenes. , 2012, Angewandte Chemie.

[5]  J. Collin,et al.  Catalytic, enantioselective intramolecular hydroamination of primary amines tethered to di- and trisubstituted alkenes. , 2011, The Journal of organic chemistry.

[6]  A. Sadow,et al.  Concerted C–N/C–H Bond Formation in Highly Enantioselective Yttrium(III)-Catalyzed Hydroamination , 2011 .

[7]  L. Schafer,et al.  Mechanistic elucidation of intramolecular aminoalkene hydroamination catalyzed by a tethered bis(ureate) complex: evidence for proton-assisted C-N bond formation at zirconium. , 2011, Journal of the American Chemical Society.

[8]  Yong Tang,et al.  Intramolecular hydroamination of aminoalkenes catalyzed by a cationic zirconium complex. , 2011, Organic letters.

[9]  A. Rheingold,et al.  Asymmetric Catalytic Intramolecular Hydroamination of Aminoallenes by Tantalum Amidoalkoxide Complexes , 2011 .

[10]  J. Collin,et al.  Easy Routes towards Chiral Lithium Binaphthylamido Catalysts for the Asymmetric Hydroamination of Amino‐1,3‐dienes and Aminoalkenes , 2011 .

[11]  Benjamin D. Ward,et al.  Chiral calcium catalysts for asymmetric hydroamination/cyclisation. , 2011, Chemical communications.

[12]  Songcheng Xu,et al.  A highly enantioselective zirconium catalyst for intramolecular alkene hydroamination: significant isotope effects on rate and stereoselectivity. , 2011, Angewandte Chemie.

[13]  P. Roesky,et al.  Chiral lutetium benzamidinate complexes. , 2011, Chemical communications.

[14]  G. L. Hamilton,et al.  Asymmetric Additions to Dienes Catalyzed by a Dithiophosphoric Acid , 2011, Nature.

[15]  A. Reznichenko,et al.  Asymmetric intermolecular hydroamination of unactivated alkenes with simple amines. , 2010, Angewandte Chemie.

[16]  G. Clarkson,et al.  Mechanism of catalytic cyclohydroamination by zirconium salicyloxazoline complexes. , 2010, Journal of the American Chemical Society.

[17]  J. Collin,et al.  Well-defined and easily accessible yttrium complexes for enantioselective cyclisation of amines tethered to 1,2-di-substituted alkenes. , 2010, Chemical communications.

[18]  T. Nugent.  Chiral amine synthesis : methods, developments and applications , 2010 .

[19]  S. Buchwald,et al.  Rhodium-catalyzed asymmetric intramolecular hydroamination of unactivated alkenes. , 2009, Angewandte Chemie.

[20]  K. Hultzsch,et al.  Intramolecular hydroamination/cyclization of aminoalkenes catalyzed by diamidobinaphthyl magnesium- and zinc-complexes , 2009 .

[21]  Guofu Zi,et al.  Synthesis of Group 4 Metal Amides with New Chiral Biaryldiamine-Based Ligands and Their Use as Catalysts for Asymmetric Hydroamination/Cyclization , 2009 .

[22]  J. Collin,et al.  Convenient method for the rapid generation of highly active and enantioselective yttrium catalysts for asymmetric hydroamination. , 2008, Chemical communications.

[23]  G. Clarkson,et al.  Catalytic alkene cyclohydroamination via an imido mechanism. , 2008, Chemical communications.

[24]  Guofu Zi,et al.  Enantioselective Hydroamination/Cyclization Catalyzed by Organolanthanide Amides Derived from a New Chiral Ligand, (S)-2-(Pyrrol-2-ylmethyleneamino)-2′-(dimethylamino)-1,1′-binaphthyl , 2008 .

[25]  J. Collin,et al.  New axially chiral atropos and tropos secondary diamines as ligands for enantioselective intramolecular hydroamination , 2008 .

[26]  K. Tomioka,et al.  Catalytic asymmetric intramolecular hydroamination of aminoalkenes , 2007 .

[27]  G. L. Hamilton,et al.  A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal Catalysis , 2007, Science.

[28]  M. Lautens,et al.  New frontiers in asymmetric catalysis , 2007 .

[29]  T. Marks,et al.  Organophosphine Oxide/Sulfide-Substituted Lanthanide Binaphtholate Catalysts for Enantioselective Hydroamination/Cyclization , 2007 .

[30]  J. Kozak,et al.  Chiral neutral zirconium amidate complexes for the asymmetric hydroamination of alkenes. , 2006, Angewandte Chemie.

[31]  R. Widenhoefer,et al.  Gold(I)-catalyzed intramolecular enantioselective hydroalkoxylation of allenes. , 2007, Angewandte Chemie.

[32]  A. Zulys,et al.  A chiral-bridged aminotroponiminate complex of lutetium as catalyst for the asymmetric hydroamination , 2006 .

[33]  F. Hampel,et al.  Base-catalysed asymmetric hydroamination/cyclisation of aminoalkenes utilising a dimeric chiral diamidobinaphthyl dilithium salt. , 2006, Chemical communications.

[34]  F. Hampel,et al.  3,3'-Bis(trisarylsilyl)-substituted binaphtholate rare earth metal catalysts for asymmetric hydroamination. , 2006, Journal of the American Chemical Society.

[35]  T. Livinghouse,et al.  Enantioselective intramolecular alkene hydroaminations catalyzed by yttrium complexes of axially chiral bis(thiolate) ligands. , 2005, Organic letters.

[36]  Adam R. Johnson,et al.  Catalytic Intramolecular Hydroamination of Substituted Aminoallenes by Chiral Titanium Amino-Alcohol Complexes , 2004 .

[37]  P. Scott,et al.  Zirconium catalysed enantioselective hydroamination/cyclisation. , 2004, Chemical communications.

[38]  J. Collin,et al.  Lanthanide complexes derived from (R)-1,1'-binaphthyl-2,2'-bis(neopentylamine)--(Li(THF)4)(Ln[(R)-C20H12N2(C10H22)]2) (Ln = Sm, Yb)--novel catalysts for enantioselective intramolecular hydroamination. , 2003, Chemical communications.

[39]  T. Marks,et al.  C2-symmetric bis(oxazolinato)lanthanide catalysts for enantioselective intramolecular hydroamination/cyclization. , 2003, Journal of the American Chemical Society.

[40]  F. Hampel,et al.  Synthesis and characterization of new biphenolate and binaphtholate rare-Earth-metal amido complexes: catalysts for asymmetric olefin hydroamination/cyclization. , 2003, Chemistry.

[41]  P. Scott,et al.  Chiral-at-metal organolanthanides: enantioselective aminoalkene hydroamination/cyclisation with non-cyclopentadienyls , 2003 .

[42]  A. Ricci.  Modern Amination Methods , 2000 .

[43]  George M. Sheldrick,et al.  SADABS, Program for Empirical Absorption Correction of Area Detector Data , 1996 .

[44]  V. Conticello,et al.  Chiral Organolanthanides Designed for Asymmetric Catalysis. Synthesis, Characterization, and Configurational Interconversions of Chiral, C1-Symmetric Organolanthanide Halides, Amides, and Hydrocarbyls , 1994 .

[45]  V. Conticello,et al.  Stereoselection Effects in the Catalytic Hydroamination/Cyclization of Amino olefins at Chiral Organolanthanide Centers , 1992 .

[46]  T. Marks,et al.  Organolanthanide-Catalyzed Hydroamination. A Kinetic, Mechanistic, and Diastereoselectivity Study of the Cyclization of N-Unprotected Amino Olefins , 1992 .

[47]  J. Schwartz,et al.  Organometallics , 1987, Science.