A class of benzene backbone-based olefin-sulfoxide ligands for Rh-catalyzed enantioselective addition of arylboronic acids to enones.

A class of readily available and easily tunable benzene backbone-based olefin-sulfoxide ligands was developed for the rhodium-catalyzed asymmetric conjugate addition reaction of arylboronic acids to enones with up to 97% yield and 97% ee.

[1]  Liangchun Li,et al.  Chiral sulfoxide-olefin ligands: completely switchable stereoselectivity in rhodium-catalyzed asymmetric conjugate additions. , 2011, Angewandte Chemie.

[2]  Hui Wang,et al.  Design of N-sulfinyl homoallylic amines as novel sulfinamide-olefin hybrid ligands for asymmetric catalysis: application in Rh-catalyzed enantioselective 1,4-additions. , 2011, Chemical communications.

[3]  Tingshun Zhu,et al.  Design of chiral sulfoxide-olefins as a new class of sulfur-based olefin ligands for asymmetric catalysis. , 2011, Organic letters.

[4]  Jing Yang,et al.  Simple N-sulfinyl-based chiral sulfur-olefin ligands for rhodium-catalyzed asymmetric 1,4-additions. , 2011, Organic letters.

[5]  P. Mayer,et al.  Sulfoxide-alkene hybrids: a new class of chiral ligands for the Hayashi-Miyaura reaction. , 2011, Organic letters.

[6]  Zhi‐Xiang Yu,et al.  α,β-Divinyl tetrahydropyrroles as chiral chain diene ligands in rhodium(I)-catalyzed enantioselective conjugated additions. , 2011, Organic Letters.

[7]  Luigi Cavallo,et al.  C2-symmetric chiral disulfoxide ligands in rhodium-catalyzed 1,4-addition: from ligand synthesis to the enantioselection pathway. , 2010, Chemistry.

[8]  H. Du,et al.  Development of chiral terminal-alkene-phosphine hybrid ligands for palladium-catalyzed asymmetric allylic substitutions. , 2010, Organic letters.

[9]  E. Corey,et al.  Catalytic enantioselective formation of chiral-bridged dienes which are themselves ligands for enantioselective catalysis. , 2010, Organic letters.

[10]  H. Du,et al.  Development of binaphthyl-based chiral dienes for rhodium(I)-catalyzed asymmetric arylation of N,N-dimethylsulfamoyl-protected aldimines. , 2010, Organic letters.

[11]  Yong‐Gui Zhou,et al.  Highly effective and diastereoselective synthesis of axially chiral bis-sulfoxide ligands via oxidative aryl coupling. , 2010, Organic Letters.

[12]  A. Carnell,et al.  Chemoenzymatic synthesis and application of bicyclo[2.2.2]octadiene ligands: increased efficiency in rhodium-catalyzed asymmetric conjugate additions by electronic tuning. , 2010, Angewandte Chemie.

[13]  Dong Li,et al.  tert‐Butanesulfinylphosphines: Simple Chiral Ligands in Rhodium‐Catalyzed Asymmetric Addition of Arylboronic Acids to Electron‐Deficient Olefins , 2010 .

[14]  Lin-feng Cun,et al.  A C(2)-symmetric chiral bis-sulfoxide ligand in a rhodium-catalyzed reaction: asymmetric 1,4-addition of sodium tetraarylborates to chromenones. , 2010, Journal of the American Chemical Society.

[15]  F. Glorius,et al.  Olefin-oxazolines (OlefOx): highly modular, easily tunable ligands for asymmetric catalysis. , 2010, Angewandte Chemie.

[16]  E. Fillion,et al.  Asymmetric addition of alkenylstannanes to alkylidene Meldrum's acids. , 2009, Organic letters.

[17]  A. Jäschke,et al.  Allylic amination by a DNA-diene-iridium(I) hybrid catalyst. , 2009, Angewandte Chemie.

[18]  Justus J. Bürgi,et al.  Unprecedented selectivity via electronic substrate recognition in the 1,4-addition to cyclic olefins using a chiral disulfoxide rhodium catalyst. , 2009, Angewandte Chemie.

[19]  J. Genêt,et al.  C1-symmetric monosubstituted chiral diene ligands in asymmetric rhodium-catalyzed 1,4-addition reactions. , 2008, Angewandte Chemie.

[20]  G. Lin,et al.  Highly practical catalytic asymmetric 1,4-addition of arylboronic acids in water using new hydrophilic chiral bicyclo[3.3.0] diene ligands. , 2008, Organic letters.

[21]  E. Carreira,et al.  Chiral olefins as steering ligands in asymmetric catalysis. , 2008, Angewandte Chemie.

[22]  X. Luan,et al.  A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins. , 2008, Journal of the American Chemical Society.

[23]  J. B. Johnson,et al.  More than bystanders: the effect of olefins on transition-metal-catalyzed cross-coupling reactions. , 2008, Angewandte Chemie.

[24]  S. P. Andrews,et al.  Enantioselective preparation of 1,1-diarylethanes: aldehydes as removable steering groups for asymmetric synthesis. , 2007, Angewandte Chemie.

[25]  M. Mellah,et al.  Chiral sulfur ligands for asymmetric catalysis. , 2007, Chemical reviews.

[26]  S. Laschat,et al.  Chiral bicyclo[3.3.0]octa-2,5-dienes as steering ligands in substrate-dependent rhodium-catalyzed 1,4-addition of arylboronic acids to enones , 2007 .

[27]  J. Christoffers,et al.  Recent Advances in Metal-Catalyzed Asymmetric Conjugate Additions , 2007 .

[28]  G. Lin,et al.  Design of C2-symmetric tetrahydropentalenes as new chiral diene ligands for highly enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids. , 2007, Journal of the American Chemical Society.

[29]  Wei-Liang Duan,et al.  Chiral phosphine-olefin ligands in the rhodium-catalyzed asymmetric 1,4-addition reactions. , 2007, Journal of the American Chemical Society.

[30]  K. Mikami,et al.  Asymmetric synergy between chiral dienes and diphosphines in cationic Rh(I)-catalyzed intramolecular [4 + 2] cycloaddition. , 2006, Journal of the American Chemical Society.

[31]  M. Wörle,et al.  Chiral phosphane alkenes (PALs): simple synthesis, applications in catalysis, and functional hemilability. , 2006, Chemistry.

[32]  J. Faller,et al.  Resolution of BIPHEP on Rh with a chiral diene auxiliary , 2006 .

[33]  Wei-Liang Duan,et al.  Chiral phosphine-olefin bidentate ligands in asymmetric catalysis: rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to maleimides. , 2005, Angewandte Chemie.

[34]  E. Carreira,et al.  Asymmetric synthesis of 3,3-diarylpropanals with chiral diene-rhodium catalysts. , 2005, Journal of the American Chemical Society.

[35]  K. Okamoto,et al.  Highly chemo- and enantioselective arylative cyclization of alkyne-tethered electron-deficient olefins catalyzed by rhodium complexes with chiral dienes. , 2005, Angewandte Chemie.

[36]  P. Maire,et al.  Chiral Rhodium(I) and Iridium(I) Amino−Olefin Complexes: pKa, N−H Bond Dissociation Energy, and Catalytic Transfer Hydrogenation , 2005 .

[37]  K. Okamoto,et al.  Catalytic asymmetric arylative cyclization of alkynals: phosphine-free rhodium/diene complexes as efficient catalysts. , 2005, Journal of the American Chemical Society.

[38]  F. Glorius.  Chiral olefin ligands-new "spectators" in asymmetric catalysis. , 2004, Angewandte Chemie.

[39]  E. Carreira,et al.  Readily available [2.2.2]-bicyclooctadienes as new chiral ligands for Ir(I): catalytic, kinetic resolution of allyl carbonates. , 2004, Journal of the American Chemical Society.

[40]  Tamio Hayashi,et al.  Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions. , 2003, Chemical reviews.

[41]  M. Ogasawara,et al.  Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids. Arylrhodium, oxa-pi-allylrhodium, and hydroxorhodium intermediates. , 2002, Journal of the American Chemical Society.

[42]  L. Mannina,et al.  Stereocontrolled synthesis of carbon–carbon double bond locked analogues of strobilurins which are characterized by a trans-1,2-disubstituted cyclopropane ring , 2001 .

[43]  N. Miyaura,et al.  Rhodium-Catalyzed Conjugate Addition of Aryl- or 1-Alkenylboronic Acids to Enones , 1997 .

[44]  R. Baker,et al.  A Convenient Modification of the Wadsworth-Emmons Method of Olefin Formation Using a Crown Ether , 1981 .

[45]  H. F. Herbrandson,et al.  Derivatives of Aromatic Sulfinic Acids. III. Evidence for the Hydrogen Dichloride Ion from Epimerization Reactions1 , 1959 .

[46]  M. Lautens,et al.  Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds. , 2003, Chemical reviews.

[47]  A. Hajipour,et al.  A convenient synthesis of 2-methoxy-1-naphthyl sulfoxides in high enantiomeric purity. A new asymmetric synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines , 1994 .