Catalysts For Fine Chemical V, Vol. 5

Series Preface     xviiPreface to Volume 5     xixAbbreviations     xxiIndustrial Catalysts for Regio- or Stereo-Selective Oxidations and Reductions A Review of Key Technologies and Targets   John Whittall     1Introduction     2Reduction of Carbon-Carbon Double Bonds     3Privileged structures: [alpha]-amino acids and itaconic acids     4[beta]-Amino acids     5[alpha]-Alkyl substituted acids     6[alpha]-Alkoxy substituted acids     8Unsaturated nitriles     9Alkenes and allyl alcohols     10[alpha],[beta]-Unsaturated aldehyde reduction     10Ketone and Imine Reduction     12Catalytic hydrogenation of ketones and imines     12Asymmetric transfer hydrogenation (ATH) catalysts     15Modified borane reagents     20Biocatalysts (alcohol dehydrogenases and ketoreductases)     21Oxidation     23Sharpless chiral epoxidation of allyl alcohols     23Dioxirane catalyzed epoxidation     23Amines and iminium salts     25Phase transfer catalysts     25The Julia-Colonna method (polyleucine oxidation)     26Organocatalytic [alpha]-hydroxylation of ketones     27Baeyer-Villiger oxidation     27Chiral sulfoxides     28References     29Asymmetric Hydrogenation of Alkenes, Enones, Ene-Esters and Ene-Acids     35(S)-2,2[prime]-Bis{lcub}[di(4-methoxyphenyl)phosphinyl]oxy{rcub}-5,5[prime],6,6[prime],7,7[prime],8,8[prime]-octahydro-1,1[prime]-binaphthyl as a ligand for rhodium-catalyzed asymmetric hydrogenation   Ildiko Gergely   Csaba Hegedus   Jozsef Bakos     36Synthesis of (S)-5,5[prime],6,6[prime],7,7[prime],8,8[prime]-Octahydro-1,1[prime]-bi-2-naphthol     37Synthesis of (S)-2,2[prime]-Bis{lcub}[di(4-methoxyphenyl)phosphinyl]oxy{rcub}-5,5[prime],6,6[prime],7,7[prime],8,8[prime]-octahydro-1,1[prime]-binaphthyl     38Asymmetric hydrogenation of Dimethyl itaconate     40Conclusion     41References     41Synthesis and application of phosphinite oxazoline iridium complexes for the asymmetric hydrogenation of alkenes   Frederik Menges   Andreas Pfaltz     42Synthesis of (4S,5S)-2-(5-Methyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-1,3-diphenyl-propan-2-ol     42Synthesis of (4S,5S)-O-[1-Benzyl-1-(5-methyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-2-phenyl-ethyl]-diphenylphosphinite     43Synthesis of (4S,5S)-[([eta superscript 4]-1,5-Cyclooctadiene)-{lcub}2-(2-phenyl-5-methyl-4,5-dihydro-oxazol-4-yl)-1,3-diphenyl-2-diphenylphosphinite-propane{rcub}iridium(I)]-tetrakis[3,5-bis(trifluoromethyl)phenyl]borate     45Asymmetric hydrogenation of trans-[alpha]-Methylstilbene     46Conclusion     47References     48Synthesis and application of heterocyclic phosphine oxazoline (HetPHOX) iridium complexes for the asymmetric hydrogenation of alkenes   Frederik Menges   Pier Giorgio Cozzi     48Synthesis of (4S)-tert-Butyl-2-(thiophene-2-yl)-4,5-dihydrooxazole     49Synthesis of (4S)-tert-Butyl-2-(3-diphenylphosphino-thiophene-2-yl)-4,5-dihydrooxazole     50Synthesis of (4S)-[([eta superscript 4]-1,5-Cyclooctadiene)-{lcub}4-tert-butyl-2-(3-diphenylphosphino-thiophene-2-yl)-4,5-dihydrooxazole{rcub}iridium(I)]-tetrakis [3,5-bis(trifluoromethyl)phenyl]borate     52Asymmetric hydrogenation of trans-[alpha]-Methylstilbene     53Conclusion     54References     54(R)-2,2[prime],6,6[prime]-Tetramethoxy-bis[di(3,5-dimethylphenyl)phosphino]-3,3[prime]-bipyridine [(R)-Xyl-P-Phos] as a ligand for rhodium-catalyzed asymmetric hydrogenation of [alpha]-dehydroamino acids   Jing Wu   Albert S.C. Chan     55Synthesis of 3-Bromo-2,6-dimethoxypyridine     55Synthesis of Bis(3,5-dimethylphenyl)phosphine chloride      56Synthesis of 3-Bromo-2,6-dimethoxy-4-di(3,5-dimethylphenyl)phosphinopyridine     57Synthesis of 3-Bromo-2,6-dimethoxy-4-di(3,5-dimethylphenyl)phosphinopyridine     592,2[prime],6,6[prime]-Tetramethoxy-bis[di(3,5-dimethylphenyl)phosphinoyl]-3,3[prime]-bipyridine     60Optical resolution of ([plus or minus])-6 with (-) or (+)-2,3-0,0[prime]-Dibenzoyltartaric acid monohydrate [(R)-6 or (S)-6)]     61(R)-2,2[prime],6,6[prime]-Tetramethoxy-bis[di(3,5-dimethylphenyl)phosphino]-3,3[prime]-bipyridine [(R)-Xyl-P-Phos, (R)-1]     62Preparation of the stock solution of [Rh(R-Xyl-P-Phos)(COD)]BF[subscript 4]     63A typical procedure for the asymmetric hydrogenation of methyl (Z)-2-Acetamidocinnamate     64References     65(R,R)-2,3-Bis(tert-butylmethylphosphino)quinoxaline (QuinoXP) as a ligand for rhodium-catalyzed asymmetric hydrogenation of prochiral amino acid and amine derivatives   Tsuneo Imamoto   Aya Koide     55Synthesis of (R)-tert-Butyl(hydroxymethyl)methylphosphine-borane     66Synthesis of (R)-Benzoyloxy(tert-butyl)methylphosphine-borane     67Synthesis of (S)-tert-Butylmethylphosphine-borane     69(R,R)-2,3-Bis(tert-butylmethylphosphino)quinoxaline (QuinoxP)     70Asymmetric hydrogenation of Methyl (E)-3-acetylamino-2-butenoate catalyzed by Rh(I)-(R,R)-2,3-Bis(tert-butylmethylphosphino)quinoxaline     71Conclusion     72References     73Rhodium-catalyzed asymmetric hydrogenation of indoles   Ryoichi Kuwano   Masaya Sawamura     73Synthesis of (R)-2-[(S)-1-(Dimethylamino)ethyl]-1-iodoferrocene     73Synthesis of (R)-2-[(S)-1-(Diphenylphosphinyl)ethyl]-1-iodoferrocene     75Synthesis of (R,R)-2,2[prime]-Bis[(S)-1-(diphenylphosphinyl)ethyl]-1,1[Prime]-biferrocene     78Synthesis of (R,R)-2,2[Prime]-Bis[(S)-1-(diphenylphosphino)ethyl]-1,1[Prime]-biferrocene [abbreviated to (S,S)-(R,R)-PhTRAP]     80Catalytic asymmetric hydrogenation of N-Acetyl-2-butylindole     82Catalytic asymmetric hydrogenation of 3-Methyl-N-(p-toluenesulfonyl)indole     84Conclusion     85References     86Asymmetric Reduction of Ketones     87(R,R)-Bis(diphenylphosphino)-1,3-diphenylpropane as a versatile ligand for enantioselective hydrogenations   Natalia Dubrovina   Armin Borner     89Synthesis of (S,S)-1,3-Diphenylpropane-1,3-diol     89Synthesis of (S,S)-Methanesulfonyloxy-1,3-diphenylpropane-1,3-diol     91Synthesis of (R,R)-Bis(diphenylphosphino)-1,3-diphenylpropane     91Conclusion      93References     93Synthesis of both enantiomers of 1-Phenylethanol by reduction of acetophenone with Geotrichum candidum IFO 5767   Kaoru Nakamura   Mikio Fujii   Yoshiteru Ida     93Cultivation of G. candidum IFO 5767     94Synthesis of (S)-1-Phenylethanol     95Synthesis of (R)-1-Phenylethanol     95Conclusion     97References     97Titanocene-catalyzed reduction of ketones in the presence of water. A convenient procedure for the synthesis of alcohols via free-radical chemistry   Antonio Rosales   Juan M. Cuerva   J. Enrique Oltra     97Titanocene-catalyzed reduction of Acetophenone in the presence of water     98Titanocene-catalyzed synthesis of Methyl 4-deuterio-4-phenyl-4-hydroxybutanoate     99References     100Xyl-tetraPHEMP: a highly efficient biaryl ligand in the [diphosphine RuCl[subscript 2] diamine]-catalyzed hydrogenation of simple aromatic ketones   Paul H. Moran   Julian P. Henschke   Antonio Zanotti-Gerosa   Ian C. Lennon     101Synthesis of Tri(3,5-dimethylphenyl)phosphine oxide     102Synthesis of Bis(3,5-dimethylphenyl)-(2-iodo-3,5-dimethylphenyl)phosphine oxide     103Synthesis of rac-4,4[prime],6,6[prime]-Tetramethyl-2,2[prime]-bis[bis(3,5-dimethylphenyl)phosphinoyl]-biphenyl     105Synthesis of rac-4,4[prime],6,6[prime]-Tetramethyl-2,2[prime]-bis[bis(3,5-dimethylphenyl)phosphino]-biphenyl [abbreviated to (rac)-Xyl-tetraPHEMP]     106Synthesis of [(R)-N,N-Dimethyl(1-methyl)benzylaminato-C[superscript 2],N]-{lcub}rac-4,4[prime],6,6[prime]-tetramethyl-2,2[prime]-bis[bis(3,5-dimethylphenyl)phosphino]-biphenyl{rcub}-palladium(II) tetrafluoroborate and separation of the diastereomers     107Synthesis of (S)-4,4[prime],6,6[prime]-Tetramethyl-2,2[prime]-bis[bis(3,5-dimethylphenyl)phosphino]-biphenyl: [abbreviated to (S)-Xyl-tetraPHEMP) and (R)-4,4[prime],6,6[prime]-Tetramethyl-2,2[prime]-bis[bis(3,5-dimethylphenyl)phosphino]-biphenyl [abbreviated to (R)-Xyl-tetraPHEMP]     108Synthesis of [(R)-Xyl-tetraPHEMP RuCl[subscript 2] (R,R)-DPEN] and [(S)-Xyl-tetraPHEMP RuCl[subscript 2] (S,S)-DPEN]     110Reduction of Acetophenone using [(S)-Xyl-tetraPHEMP RuCl[subscript 2] (S,S)-DPEN] as a precatalyst     111Conclusion     112References     112N-Arenesulfonyl- and N-Alkylsulfamoyl-1,2-diphenylethylenediamine ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of activated ketones   Michel (Massoud S.) Stephan   Barbara Mohar     113Synthesis of N-Arenesulfonyl-1,2-diphenylethylenediamines     113Preparation of Ru(II)-N-arenesulfonyl-1,2-diphenylethylenediamine complexes     114Asymmetric transfer hydrogenation of Ethyl benzoylacetate     115Conclusion     116References     116The synthesis and application of BrXuPHOS: a novel monodentate phosphorus ligand for the asymmetric hydrogenation of ketones   Martin Wills   Yingjian Xu   Garden Docherty   Gary Woodward     116Synthesis of (S)-BrXuPHOS     117Synthesis of (S,S,SS)-BrXuPHOS-Ru-DPEN     119General procedure of asymmetric hydrogenation of acetophenone     120Conclusion     121Acknowledgement     121References     121In Situ formation of ligand and catalyst: application in ruthenium-catalyzed enantioselective reduction of ketones   Jenny Wettergren   Hans Adolfsson     121Synthesis of (S)-3-Fluoro-1-phenylethanol     122Conclusion     123References     124Synphos and Difluorphos as ligands for ruthenium-catalyzed hydrogenation of alkenes and ketones   Severine Jeulin   Virginie Ratovelomanana-Vidal   Jean-Pierre Genet     125Synthesis of [RuCl((S)-SYNPHOS)(p-cymene)]Cl     125Synthesis of [RuCl((S)-DIFLUORPHOS)(p-cymene)]Cl     126Synthesis of [RuI((S)-DIFLUORPHOS)(p-cymene)]I     127Synthesis of [NH[subscript 2]R[subscript 2]] [(RuCl(PP))[subscript 2]([Mu]-Cl)[subscript 3]] PP = SYNPHOS or DIFLUORPHOS and R = Me or Et     127Synthesis of [NH[subscript 2]Me[subscript 2]][RuCl-(S)-DIFLUORPHOS][subscript 2][[Mu]-Cl][subscript 3]     128Synthesis of in situ generated [RuBr[subscript 2]((S)-SYNPHOS)] and [RuBr[subscript 2]((S)-DIFLUORPHOS)]     129Conclusion     131References     131An arene ruthenium complex with polymerizable side chains for the synthesis of immobilized catalysts   Estelle Burri   Silke B. Wendicke   Kay Severin     132Synthesis of 2-Methyl-cyclohexa-2,5-dienecarboxylic acid 2-(2-methyl-acryloyloxy)-ethyl ester     133Synthesis of [[eta superscript 6]-(2-Methyl-benzoic acid 2-(2-methyl-acryloyloxy)-ethyl ester)RuCl[subscript 2]][subscript 2]     134Conclusion     135References     135Selective reduction of carbonyl group in [beta], [gamma]-unsaturated [alpha]-alpha-ketoesters by transfer hydrogenation with Ru-(p-cymene) (TsDPEN)   Minjie Guo   Dao Li   Yanhui Sun   Zhaoguo Zhang     135Synthesis of Di-[Mu]-chloro-bis[chloro([eta superscript 6]-1-isopropyl-4-methyl-benzene)ruthenium(II)     136Synthesis of ([plus or minus])-Monotosylate-1,2-diphenyl-1,2-ethylenediamine     136Synthesis of Ru complex Ru(p-cymene)(TsDPEN)     138Ru-TsDPEN catalyzed transfer hydrogenation reaction of [beta],[gamma]-unsaturated-[alpha]-ketoesters     139Conclusion     140References     141Preparation of polymer-supported Ru-TsDPEN catalysts and their use for the enantioselective synthesis of (S)-fluoxetine   Liting Chai   Yangzhou Li   Quanrui Wang     141Synthesis of the supported ligand 9     141Synthesis of ligand 17     148General procedure for asymmetric transfer hydrogenation     150Preparation of (S)-Fluoxetine hydrochloride     151Conclusion     154References     154Polymer-supported chiral sulfonamide-catalyzed reduction of [beta]-keto nitriles: a practical synthesis of (R)-Fluoxetine   Guang-yin Wang   Gang Zhao     155Synthesis of (R)-3-Amino-1-phenyl-propan-1-ol     155Synthesis of (R)-ethyl 3-hydroxy-3-phenylpropylcarbamate     156Synthesis of (R)-3-(Methylamino)-1-phenylpropan-1-ol     157Synthesis of (R)-Fluoxetine     158Conclusion     159References     159Imine Reduction and Reductive Amination      161Metal-free reduction of imines: enantioselective Bronsted acid-catalyzed transfer hydrogenation using chiral BINOL-phosphates as catalysts   Magnus Rueping   Erli Sugiono   Cengiz Azap   Thomas Theissmann     162Synthesis of (R)-2,2[prime]-Bis-methoxymethoxy-[1,1[prime]] binaphthalene (MOM-BINOL)     162Synthesis of (R)-3,3[prime]-Diiodo-2,2[prime]-bis(methoxymethoxy)-1,1[prime]-binaphthalene     164Synthesis of 3,3[prime]-Bis-(3,5[prime]-bis-trifluoromethyl-phenyl)-2,2[prime]-bismethoxymethoxy [1,1[prime]-binaphthalene]     165Synthesis of (R)-3,3[prime]-[3,5-Bis(trifluoromethyl)phenyl]-1,1[prime]-binaphthylphosphate     166General procedure for the transfer hydrogenation of ketimines     167Synthesis of [1-(2,4-Dimethyl-phenyl)-ethyl]-(4-methoxy-phenyl)-amine     167Conclusion     168References     170Metal-free Bronsted acid-catalyzed transfer hydrogenation: enantioselective synthesis of tetrahydroquinolines   Magnus Rueping   Thomas Theissmann   Andrey P. Antonchick     170General procedure for the transfer hydrogenation of quinolines     170Synthesis of 7-Chloro-4-phenyl-1,2,3,4-tetrahydroquinoline     172Synthesis of (S)-2-Phenyl-1,2,3,4-tetrahydroquinoline     172Synthesis of (R)-2-(2-(Benzo[1,3]dioxol-5-yl)ethyl)-1,2.3,4-tetrahydro-quinoline     173Conclusion     174References     174A highly stereoselective synthesis of 3[alpha]-Amino-23,24-bisnor-5[alpha]-cholane via reductive amination   Sharaf Nawaz Khan   Nam Ju Cho   Hong-Seok Kim     175Synthesis of Tris[(2-ethylhexanoyl)oxy]borohydride     177Synthesis of 3[alpha]-Acetamino-23,24-bisnor-5[alpha]-cholane     177Synthesis of 3[alpha]-N-1-[N(3-[4-Aminobutyl])-1,3-diaminopropane]-23,24-bisnor-5[alpha]-cholane     179Conclusion     181Acknowledgements     181References     181Oxidation of Primary and Secondary Alcohols     183Copper(Il) catalyzed oxidation of primary alcohols to aldehydes with atmospheric oxygen   Suribabu Jammi   Tharmalingan Punniyamurthy     183Synthesis of copper(II) complex 1     184Typical procedure for the oxidation of primary alcohols to aldehydes     185Conclusion     186References     187Solvent-free dehydrogenation of secondary alcohols in the absence of hydrogen abstractors using Robinson's catalyst   G.B.W.L Ligthart   R.H. Meijer   J. v. Buijtenen   J. Meuldijk   J.A.J.M. Vekemans   L.A. Hulshof     187Dehydrogenation of 2-Octanol using Ru(OCOCF[subscript 3])[subscript 2](CO)(PPh[subscript 3])[subscript 2] as a catalyst     187Conclusion     188References     1882-Iodoxybenzoic acid (IBX)/n-Bu[subscript 4]NBr/CH[subscript 2]Cl[subscript 2]-H[subscript 2]O: a mild system for the selective oxidation of secondary alcohols   Krisada Kittigowittana   Manat Pohmakotr   Vichai Reutrakul   Chutima Kuhakarn     188Synthesis of 1-Hydroxy-5-decanone     189Conclusion     192References     192Hydroxylation, Epoxidation and Related Reactions     193Proline-catalyzed [alpha]-aminoxylation of aldehydes and ketones   Yujiro Hayashi   Mitsuru Shoji     194Synthesis of (R)-2-Anilinoxypropanol     195Synthesis of (R)-7-Anilinoxy-1,4-dioxaspiro[4.5]decan-8-one     196Conclusion     197References     198Ru/Silia Cat TEMPO-mediated oxidation of alkenes to [alpha]-hydroxyacids   Rosaria Ciriminna   Mario Pagliaro     199Synthesis of Silia Cat TEMPO     199Synthesis of 2-(4-Chlorophenyl)-1,2-propanediol     201Synthesis of 2-(4-Chlorophenyl)-1,2-hydroxypropanoic acid      202Conclusion     204References     204Catalytic enantioselective epoxidation of trans-disubstituted and trisubstituted alkenes with arabinose-derived ulose   Tony K. M. Shing   Gulice Y.C. Leung   To Luk     204Synthesis of 2[prime],3[prime]-Diisobutyl acetal     205Synthesis of ulose     206Asymmetric epoxidation of trans-[alpha]-Methylstilbene using ulose as catalyst at 0 [degree]C     208Conclusion     209References     210VO(acac)[subscript 2]/TBHP catalyzed epoxidation of 2-(2-Alkenyl)phenols. highly regio- and diastereoselective oxidative cyclisation to 2,3-Dihydrobenzofuranols and 3-Chromanols   Alessandra Lattanzi   Arrigo Scettri     211VO(acac)[subscript 2]/TBHP catalyzed epoxidation of 2-(3,7-Dimethyl-octa-2,6-dienyl)-phenol     212VO(acac)[subscript 2]/TBHP/TFA catalyzed oxidative cyclization of 2-(3,7-Dimethyl-octa-2,6-dienyl)-phenol     213Conclusion     214References     214An Oxalolidinone ketone catalyst for the asymmetric epoxidation of cis-olefins   David Goeddel   Yian Shi     215Amadori rearrangement to give 1-Dibenzylamino-1-deoxy-D-fructose     215Acetal protection of 1-Dibenzylamino-1-deoxy-D-fructose      216Hydrogenation of the Dibenzylamine     217Phosgene cyclization of aminoalcohol     218Alcohol oxidation     220Synthesis of ketone 2     221Asymmetric epoxidation of cis-[beta]-Methylstyrene     222Conclusion     223References     224[alpha]-Fluorotropinone immobilised on silica: a new stereoselective heterogeneous catalyst for epoxidation of alkenes with oxone   Giovanni Sartori   Alan Armstrong   Raimondo Maggi   Alessandro Mazzacani   Raffaella Sartorio   France Bigi   Belen Dominguez-Fernandez     225Synthesis of silica KG-60-supported enantiomerically enriched [alpha]-Fluorotropinone     225Synthesis of enantiomerically enriched epoxides     226Conclusion     227References     228Asymmetric epoxidation catalyzed by novel azacrown ether-type chiral quaternary ammonium salts under phase-transfer catalytic conditions   Kazushige Hori   Keita Tani   Yasuo Tohda     228Synthesis of precursor of the azacrown ether     229Synthesis of the azacrown ether     230Synthesis of the azacrown ether-type quaternary ammonium salt     232Asymmetric epoxidation of (E)-Chalcone catalyzed by the azacrown ether-type quaternary ammonium salt as chiral PTC     233Conclusion     234References     235Enantioselective epoxidation of olefins using phase transfer conditions and a chiral [azepinium][TRISPHAT] salt as catalyst   Jerome Vachon   Celine Perollier   Alexandre Martinez   Jerome Lacour     235Enantioselective epoxidation of 1-Phenyl-3,4-dihydronaphthalene     236Conclusion     238References     239Catalytic asymmetric epoxidation of [alpha],[beta]-unsaturated esters promoted by a Yttrium-biphenyldiol complex   Masakatsu Shibasaki   Hiroyuki Kakei   Shigeki Matsunaga     239Synthesis of (aS,R)-6,6[prime]-[(Propylene)dioxy]biphenyl-2,2[prime]-diol     240Synthesis of (aS,R)-2,2-[Oxybis(ethylene)dioxy]-6,6[prime]-[(propylene)dioxy]biphenyl     242Synthesis of (S)-6,6[prime]-[Oxybis(ethylene)dioxy]biphenyl-2,2[prime]-diol     243Enantiomeric enrichment of (S)-6,6[prime]-[Oxybis(ethylene)dioxy]biphenyl-2,2[prime]-diol     244Catalytic asymmetric epoxidation of [alpha],[beta]-unsaturated esters     246References     248Catalytic enantioselective epoxidation of [alpha],[beta]-enones with a binol-zinc-complex   Ana Minatti   Karl Heinz Dotz      249Synthesis of (E)-(2S,3R)-Phenyl-(3-phenyloxiran-2-yl)methanone     249Conclusion     250References     251Asymmetric epoxidation of Phenyl-2-(3[prime]-pyridylvinyl)sulfone using polyleucine hydrogen peroxide gel   Mike R. Pitts   John Whittall     251Preparation of polyleucine-hydrogen peroxide gel     252Synthesis of Phenyl-2-(3[prime]-pyridylvinyl) sulfone (2)     252References     254Oxidation of Ketones to Lactones or Enones     255Synthesis of 2-(Phosphinophenyl)pyrindine ligand and its application to palladium-catalyzed asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones   Katsuji Ito   Tsutomu Katsuki     256Synthesis of (7R)-2-(2-Hydroxyphenyl)-7-isopropyl-6,7-dihydro-5H-1-pyrindine     2562-[2-(Diphenylphosphinoyl)phenyl]-7-isopropyl-6,7-dihydro-5H-1-pyrindine     2582-[2-(Diphenylphosphanyl)phenyl]-7-isopropyl-6,7-dihydro-5H-1-pyrindine     259Asymmetric Baeyer-Villiger oxidation of 3-Phenylcyclobutanone     261Conclusion     262References     263(D)-Codeinone from (D)-Dihydrocodeinone via the use of modified o-iodoxybenzoic acid (IBX). A convenient oxidation of ketones to enones   Paul Mather   John Whittall      263Synthesis of IBX     264Synthesis of codeinone     264References     266Oxidative C-C Coupling     267Enantioselective oxidative coupling of 2-Naphthols catalyzed by a novel chiral vanadium complex   Nan-Sheng Xie   Quan-Zhong Liu   Zhi-Bin Luo   Liu-Zhu Gong   Ai-Qiao Mi   Yao-Zhong Jiang     267Synthesis of 3,3-Diformyl-2,2[prime]-biphenol     268Synthesis of chiral vanadium complexes     270Catalytic oxidative coupling of 7-Alkoxy-1-naphthols by chiral vanadium complexes     271Reference     272Catalytic oxidative cross-coupling reaction of 2-Naphthol derivatives   Shigeki Habaue   Tomohisa Temma     273Synthesis of Methyl 2,2[prime]-dihydroxy-1,1[prime]-binaphthalene-3-carboxylate     273Conclusion     274References     275Oxidative coupling of benzenes with [alpha],[beta]-unsaturated aldehydes by Pd(OAc)[subscript 2]/ HPMoV/ O[subscript 2] system   Tomoyuki Yamada   Satoshi Sakaguchi   Yasutaka Ishii     275Synthesis of Cinnamaldehyde     276Conclusion     278References     278Oxidation of Sulfides and Sulfoxides      279The first example of direct oxidation of sulfides to sulfones by an osmate-molecular oxygen system   Boyapati M. Choudary   Chinta Reddy   V. Reddy   Billakanti V. Prakash   Mannepalli L. Kantam   B. Sreedhar     280Synthesis of osmate exchanged Mg-Al layered double hydroxides (LDH-OsO[subscript 4])     280Synthesis of Methyl phenyl sulfone or Methylsulfonylbenzene     281Conclusion     282References     283Selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide in the presence of zirconium tetrachloride   Kiumar Bahrami     283Oxidation of Benzyl 4-bromobenzyl sulfide to Benzyl 4-bromobenzyl sulfoxide using H[subscript 2]O[subscript 2] in the presence of zirconium tetrachloride     284Oxidation of Benzyl 4-bromobenzyl sulfide to Benzyl 4-bromobenzyl sulfone using H[subscript 2]O[subscript 2] in the presence of zirconium tetrachloride     286Conclusion     287References     287WO[subscript 3]-30 % H[subscript 2]O[subscript 2]-cinchona alkaloids: a new heterogeneous catalytic system for asymmetric oxidation and kinetic resolution of racemic sulfoxides   Vinay V. Thakur   A. Sudalai     288Synthesis of (R)-2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimadazole {lcub}(R)-(+)-Lansoprazole{rcub}     288Synthesis of (R)-(+)-Phenyl benzyl sulfoxide     290Conclusion     293References     293Benzyl-4,6-O-isopropylidene-[alpha]-(D)-glucopyranoside, 2-deoxy-2-[[(2-hydroxy-3,5-di-tert-butylphenyl)methylene]amino] as a ligand for vanadium-catalyzed asymmetric oxidation of sulfides   Raffaella Del Litto   Guiseppina Roviello   Francesco Ruffo     293Synthesis of Benzyl-4,6-O-isopropylidene-[alpha]-D-glucopyranoside, 2-deoxy-2-[[(2-hydroxy-3,5-di-tert-butylphenyl)methylene]imine]     294Oxidation of Thioanisole     295Conclusion     296References     296Asymmetric sulfoxidation of aryl methyl sulfides with hydrogen peroxide in water   Alessando Scarso   Giorgio Strukul     297Synthesis of complex (R)-BINAP)PtCl[subscript 2]     298Synthesis of complex [((R)-BINAP)Pt((OH)][subscript 2](BF[subscript 4])[subscript 2]     299Stereoselective catalytic oxidation of aryl methyl sulfides     300Conclusion     300References     301Index     303