1-Alkoxy-2,5-diphenylphospholane and -phospholanium Salts in Rhodium-Catalyzed Asymmetric Hydrogenation

A series of chiral enantiopure phosphinites was synthesized in four steps starting from phosphinic acid. New species were obtained as alkoxyphosphonium compounds. They can be used in the asymmetric hydrogenation of functionalized alkenes. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

[1]  T. V. RajanBabu,et al.  Tunable phosphinite, phosphite and phosphoramidite ligands for the asymmetric hydrovinylation reactions , 2005 .

[2]  M. Reetz,et al.  Mixtures of configurationally stable and fluxional atropisomeric monodentate P ligands in asymmetric Rh-catalyzed olefin hydrogenation. , 2005, Angewandte Chemie.

[3]  C. Claver,et al.  Furanoside thioetherphosphinite ligands for Pd-catalyzed asymmetric allylic substitution reactions , 2005 .

[4]  J. Fiaud,et al.  Chiral 1,2,5-triphenylphospholanium tetrafluoroborate as ligand precursor in Rh-catalyzed asymmetric hydrogenation of methyl (Z)-2-acetamidocinnamate , 2004 .

[5]  P. Andersson,et al.  Rationally designed ligands for asymmetric iridium-catalyzed hydrogenation of olefins. , 2004, Journal of the American Chemical Society.

[6]  C. Bruneau,et al.  Chiral Monodentate Phosphorus Ligands for Rhodium-Catalyzed Asymmetric Hydrogenation , 2004 .

[7]  M. Reetz,et al.  Mixtures of chiral monodentate phosphites, phosphonites and phosphines as ligands in Rh-catalyzed hydrogenation of N-acyl enamines: extension of the combinatorial approach , 2004 .

[8]  B. R. Steele,et al.  Rhodium complexes possessing S-phosphinite ligands with or without an amino group: application to hydroformylation of styrene , 2004 .

[9]  Garrett S Hoge.  Synthesis of both enantiomers of a P-chirogenic 1,2-bisphospholanoethane ligand via convergent routes and application to rhodium-catalyzed asymmetric hydrogenation of CI-1008 (pregabalin). , 2003, Journal of the American Chemical Society.

[10]  T. Imamoto,et al.  Recent Developments in Catalytic Asymmetric Hydrogenation Employing P‐Chirogenic Diphosphine Ligands , 2003 .

[11]  A. Alexakis,et al.  Tandem copper-catalyzed enantioselective allylation-metathesis. , 2002, Organic letters.

[12]  I. Manners,et al.  Synthesis, characterization and thermolysis of phosphinite–borane adducts: investigation of an unusual thermally-induced phenol elimination reaction , 2002 .

[13]  M. Rivard,et al.  Synthesis and first applications of a new family of chiral monophosphine ligand: 2,5-diphenylphosphospholanes , 2002 .

[14]  Xumu Zhang,et al.  Synthesis of novel chiral binaphthyl phosphorus ligands and their applications in Rh-catalyzed asymmetric hydrogenation , 2002 .

[15]  A. Chan,et al.  Easily accessible chiral amino-phosphinite ligands for highly enantioselective palladium-mediated allylic alkylation , 2002 .

[16]  A. Pfaltz,et al.  A New Class of Modular Phosphinite—Oxazoline Ligands: Ir-Catalyzed Enantioselective Hydrogenation of Alkenes. , 2002 .

[17]  A. Pfaltz,et al.  Threonine‐Derived Phosphinite‐Oxazoline Ligands for the Ir‐Catalyzed Enantioselective Hydrogenation , 2002 .

[18]  C. Richards,et al.  Simple phosphinite–oxazoline ligands for asymmetric catalysis , 2001 .

[19]  A. Börner,et al.  New Phosphorus Ligands for the Rhodium-Catalyzed Isomerization/Hydroformylation of Internal Octenes. , 2001, Angewandte Chemie.

[20]  M. Reetz,et al.  Highly Enantioselective Rh-Catalyzed Hydrogenation Reactions Based on Chiral Monophosphite Ligands. , 2000, Angewandte Chemie.

[21]  P. Laurent,et al.  Phosphane and Bis(phosphane) Ligands from Phosphinic Acids , 2000 .

[22]  M. Reetz,et al.  Rhodium-catalyzed enantioselective hydrogenation using chiral monophosphonite ligands , 2000 .

[23]  H. Kagan,et al.  Chiral monophosphines as ligands for asymmetric organometallic catalysis. , 2000, Chemical & pharmaceutical bulletin.

[24]  Louis J. Farrugia,et al.  WinGX suite for small-molecule single-crystal crystallography , 1999 .

[25]  J. Fiaud,et al.  Enantiomerically pure 1,2,5-triphenylphospholane through the synthesis and resolution of the chiral trans-(2,5)-diphenylphospholanic acid , 1999 .

[26]  J. Holz,et al.  Borane Complexes of Trivalent Organophosphorus Compounds. Versatile Precursors for the Synthesis of Chiral Phosphine Ligands for Asymmetric Catalysis , 1998 .

[27]  J. Majoral,et al.  [Cp2ZrHCl]n a useful reducing agent in phosphorus chemistry , 1997 .

[28]  T. Livinghouse,et al.  An efficient procedure for the synthesis of C-chiral bisphosphines , 1995 .

[29]  R. Noyori,et al.  Asymmetric catalysis in organic synthesis , 1994 .

[30]  I. Ojima,et al.  Catalytic Asymmetric Synthesis , 1993 .

[31]  H. Brisset,et al.  Phosphine-borane complexes; direct use in asymmetric catalysis , 1993 .

[32]  J. Legros,et al.  Preparation of optically pure 1,2,5-triphenylphospholane. Use as ligand for enantioselective transition-metal catalysis. , 1991 .

[33]  Kazuhiko Sato,et al.  Synthesis and reactions of phosphine-boranes. Synthesis of new bidentate ligands with homochiral phosphine centers via optically pure phosphine-boranes , 1990 .

[34]  T. Wada,et al.  A FACILE CONVERSION OF DIALKYL PHOSPHONATES TO DIALKYL PHOSPHORODITHIOATES , 1990 .

[35]  M. Sekine,et al.  2-cyanoethyl nucleoside 3′-phosphonates as a novel starting materials for oligonucleotide synthesis , 1988 .

[36]  H. Brunner,et al.  Asymmetric catalyses: XXXIII. New optically active phospholanes derived from tartaric acid , 1987 .

[37]  G. Röschenthaler,et al.  Halogen[2,2,2-trifluor-1-(trifluormethyl)-1-(trimethylsiloxy)-ethyl]phosphane , 1985 .

[38]  Kazuhiko Sato,et al.  Phosphine oxides and lithium aluminum hydride-sodium borohydride-cerium(III) chloride: synthesis and reactions of phosphine-boranes , 1985 .

[39]  P. Wisian-Neilson,et al.  Synthesis and reactivity of [bis(trimethylsilyl)methylene]mesitylphosphine , 1985 .

[40]  K. L. Marsi.  Mechanisms and stereochemistry of displacement of methoxide ion by hydroxide ion from phosphorus in phospholanium and phosphorinanium salts , 1975 .