Chiral olefin-sulfoxide as ligands for rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to unsaturated esters.

An efficient rhodium/olefin-sulfoxide catalyzed asymmetric conjugate addition of organoboronic acids to various unsaturated esters has been developed, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have been shown to be highly effective, and are especially applicable to unsaturated methyl esters with up to 99% yield and 91% ee.

[1]  Hui Wang,et al.  Simple branched sulfur-olefins as chiral ligands for Rh-catalyzed asymmetric arylation of cyclic ketimines: highly enantioselective construction of tetrasubstituted carbon stereocenters. , 2013, Journal of the American Chemical Society.

[2]  Tingshun Zhu,et al.  Rhodium-catalyzed enantioselective addition to unsymmetrical α-diketones: tandem one-pot synthesis of optically active 3-tetrasubstituted isochroman derivatives. , 2013, Chemistry.

[3]  Xiangqing Feng,et al.  Rhodium-catalyzed asymmetric formal cycloadditions of racemic butadiene monoxide with imines. , 2012, Organic letters.

[4]  G. Pattison,et al.  Enantioselective Rh(I)-catalyzed cyclization of arylboron compounds onto ketones. , 2012, Organic letters.

[5]  Tingshun Zhu,et al.  Rhodium-catalyzed, highly enantioselective 1,2-addition of aryl boronic acids to α-ketoesters and α-diketones using simple, chiral sulfur-olefin ligands. , 2012, Angewandte Chemie.

[6]  Jing Yang,et al.  Rh(I)-catalyzed asymmetric 1,2-addition to α-diketones with chiral sulfur-alkene hybrid ligands. , 2012, Organic letters.

[7]  G. Lin,et al.  Rhodium-Catalyzed Asymmetric Arylation , 2012 .

[8]  Xiangqing Feng,et al.  Kinetic resolution of hindered Morita-Baylis-Hillman adducts by Rh(I)-catalyzed asymmetric 1,4-addition/β-hydroxyelimination. , 2011, Organic letters.

[9]  F. Xue,et al.  A class of benzene backbone-based olefin-sulfoxide ligands for Rh-catalyzed enantioselective addition of arylboronic acids to enones. , 2011, The Journal of organic chemistry.

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

[11]  G. Lin,et al.  Highly enantioselective arylation of N-tosylalkylaldimines catalyzed by rhodium-diene complexes. , 2011, Journal of the American Chemical Society.

[12]  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.

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

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

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

[16]  R. Shintani,et al.  Rhodium-catalyzed asymmetric addition of potassium organotrifluoroborates to N-sulfonyl ketimines. , 2011, Organic letters.

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

[18]  Jeremiah S. Duncan,et al.  Selective syntheses of iron-imide-sulfide cubanes, including a partial representation of the Fe-S-X environment in the FeMo cofactor. , 2010, Journal of the American Chemical Society.

[19]  R. Shintani,et al.  Rhodium-catalyzed asymmetric arylation of N-tosyl ketimines. , 2010, Journal of the American Chemical Society.

[20]  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.

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

[22]  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.

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

[24]  R. F. Jordan,et al.  Self-assembled tetranuclear palladium catalysts that produce high molecular weight linear polyethylene. , 2010, Journal of the American Chemical Society.

[25]  H. Du,et al.  Simple chiral chain dienes as ligands for Rh(I)-catalyzed conjugated additions. , 2009, Organic letters.

[26]  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.

[27]  J. Tunge,et al.  A homogeneous, recyclable rhodium(I) catalyst for the hydroarylation of Michael acceptors. , 2009, Organic letters.

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

[29]  K. Okamoto,et al.  Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions. , 2008, Organic letters.

[30]  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.

[31]  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.

[32]  K. Okamoto,et al.  Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to arylmethylene cyanoacetates. , 2008, Organic letters.

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

[34]  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.

[35]  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.

[36]  Yasunori Yamamoto,et al.  1,4-Addition of arylboronic acids to β-aryl-α,β-unsaturated ketones and esters catalyzed by a rhodium(I)–chiraphos complex for catalytic and enantioselective synthesis of selective endothelin A receptor antagonists , 2006 .

[37]  E. Carreira,et al.  Catalytic asymmetric synthesis with rh-diene complexes: 1,4-addition of arylboronic acids to unsaturated esters. , 2005, Organic letters.

[38]  E. Carreira,et al.  Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range of acceptors. , 2004, Organic letters.

[39]  M. Lautens,et al.  Rhodium-Catalyzed Heck-Type Coupling of Boronic Acids with Activated Alkenes in an Aqueous Emulsion , 2004 .

[40]  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.

[41]  N. Tokunaga,et al.  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. , 2003, Journal of the American Chemical Society.

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

[43]  Jianhua Xie,et al.  1,6-Asymmetric Induction during the Conjugate Addition of Arylcopper Reagents to Chiral Sulfinyl-substituted Pyrrolyl α,β-Unsaturated Enones , 2002 .

[44]  Tamio Hayashi.  Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids and Their Derivatives to Electron Deficient Olefins , 2001 .

[45]  R. K. Smith,et al.  Highly stereoselective addition of organolithium reagents to chiral oxazolines. Asymmetric synthesis of 3-substituted alkanoic acids and 3-substituted lactones , 1979 .

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