John WhittallIldiko Gergely and Csaba Hegedus and Jozsef BakosFrederik Menges and Andreas PfaltzFrederik Menges and Pier Giorgio CozziJing Wu and Albert S.C. ChanTsuneo Imamoto and Aya KoideRyoichi Kuwano and Masaya SawamuraNatalia Dubrovina and Armin BornerKaoru Nakamura and Mikio Fujii and Yoshiteru IdaAntonio Rosales and Juan M. Cuerva and J. Enrique OltraPaul H. Moran and Julian P. Henschke and Antonio Zanotti-Gerosa and Ian C. LennonMichel (Massoud S.) Stephan and Barbara MoharMartin Wills and Yingjian Xu and Garden Docherty and Gary WoodwardJenny Wettergren and Hans AdolfssonSeverine Jeulin and Virginie Ratovelomanana-Vidal and Jean-Pierre GenetEstelle Burri and Silke B. Wendicke and Kay SeverinMinjie Guo and Dao Li and Yanhui Sun and Zhaoguo ZhangLiting Chai and Yangzhou Li and Quanrui WangGuang-yin Wang and Gang ZhaoMagnus Rueping and Erli Sugiono and Cengiz Azap and Thomas TheissmannMagnus Rueping and Thomas Theissmann and Andrey P. AntonchickSharaf Nawaz Khan and Nam Ju Cho and Hong-Seok KimSuribabu Jammi and Tharmalingan PunniyamurthyG.B.W.L Ligthart and R.H. Meijer and J. v. Buijtenen and J. Meuldijk and J.A.J.M. Vekemans and L.A. HulshofKrisada Kittigowittana and Manat Pohmakotr and Vichai Reutrakul and Chutima KuhakarnYujiro Hayashi and Mitsuru ShojiRosaria Ciriminna and Mario PagliaroTony K. M. Shing and Gulice Y.C. Leung and To LukAlessandra Lattanzi and Arrigo ScettriDavid Goeddel and Yian ShiGiovanni Sartori and Alan Armstrong and Raimondo Maggi and Alessandro Mazzacani and Raffaella Sartorio and France Bigi and Belen Dominguez-FernandezKazushige Hori and Keita Tani and Yasuo TohdaJerome Vachon and Celine Perollier and Alexandre Martinez and Jerome LacourMasakatsu Shibasaki and Hiroyuki Kakei and Shigeki MatsunagaAna Minatti and Karl Heinz DotzMike R. Pitts and John WhittallKatsuji Ito and Tsutomu KatsukiPaul Mather and John WhittallNan-Sheng Xie and Quan-Zhong Liu and Zhi-Bin Luo and Liu-Zhu Gong and Ai-Qiao Mi and Yao-Zhong JiangShigeki Habaue and Tomohisa TemmaTomoyuki Yamada and Satoshi Sakaguchi and Yasutaka IshiiBoyapati M. Choudary and Chinta Reddy and V. Reddy and Billakanti V. Prakash and Mannepalli L. Kantam and B. SreedharKiumar BahramiVinay V. Thakur and A. SudalaiRaffaella Del Litto and Guiseppina Roviello and Francesco RuffoAlessando Scarso and Giorgio Strukul

Series Preface	p. xvii
Preface to Volume 5	p. xix
Abbreviations	p. xxi
1 Industrial Catalysts for Regio- or Stereo-Selective Oxidations and Reductions A Review of Key Technologies and Targets	p. 1
1.1 Introduction	p. 2
1.2 Reduction of Carbon-Carbon Double Bonds	p. 3
1.2.1 Privileged structures: [alpha]-amino acids and itaconic acids	p. 4
1.2.2 [beta]-Amino acids	p. 5
1.2.3 [alpha]-Alkyl substituted acids	p. 6
1.2.4 [alpha]-Alkoxy substituted acids	p. 8
1.2.5 Unsaturated nitriles	p. 9
1.2.6 Alkenes and allyl alcohols	p. 10
1.2.7 [alpha],[beta]-Unsaturated aldehyde reduction	p. 10
1.3 Ketone and Imine Reduction	p. 12
1.3.1 Catalytic hydrogenation of ketones and imines	p. 12
1.3.2 Asymmetric transfer hydrogenation (ATH) catalysts	p. 15
1.3.3 Modified borane reagents	p. 20
1.3.4 Biocatalysts (alcohol dehydrogenases and ketoreductases)	p. 21
1.4 Oxidation	p. 23
1.4.1 Sharpless chiral epoxidation of allyl alcohols	p. 23
1.4.2 Dioxirane catalyzed epoxidation	p. 23
1.4.3 Amines and iminium salts	p. 25
1.4.4 Phase transfer catalysts	p. 25
1.4.5 The Julia-Colonna method (polyleucine oxidation)	p. 26
1.4.6 Organocatalytic [alpha]-hydroxylation of ketones	p. 27
1.4.7 Baeyer-Villiger oxidation	p. 27
1.4.8 Chiral sulfoxides	p. 28
References	p. 29
2 Asymmetric Hydrogenation of Alkenes, Enones, Ene-Esters and Ene-Acids	p. 35
2.1 (S)-2,2[prime]-Bis{{[di(4-methoxyphenyl)phosphinyl]oxy}}-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	p. 36
2.1.1 Synthesis of (S)-5,5[prime],6,6[prime],7,7[prime],8,8[prime]-Octahydro-1,1[prime]-bi-2-naphthol	p. 37
2.1.2 Synthesis of (S)-2,2[prime]-Bis{{[di(4-methoxyphenyl)phosphinyl]oxy}}-5,5[prime],6,6[prime],7,7[prime],8,8[prime]-octahydro-1,1[prime]-binaphthyl	p. 38
2.1.3 Asymmetric hydrogenation of Dimethyl itaconate	p. 40
Conclusion	p. 41
References	p. 41
2.2 Synthesis and application of phosphinite oxazoline iridium complexes for the asymmetric hydrogenation of alkenes	p. 42
2.2.1 Synthesis of (4S,5S)-2-(5-Methyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-1,3-diphenyl-propan-2-ol	p. 42
2.2.2 Synthesis of (4S,5S)-O-[1-Benzyl-1-(5-methyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-2-phenyl-ethyl]-diphenylphosphinite	p. 43
2.2.3 Synthesis of (4S,5S)-[([eta superscript 4]-1,5-Cyclooctadiene)-{{2-(2-phenyl-5-methyl-4,5-dihydro-oxazol-4-yl)-1,3-diphenyl-2-diphenylphosphinite-propane}}iridium(I)]-tetrakis[3,5-bis(trifluoromethyl)phenyl]borate	p. 45
2.2.4 Asymmetric hydrogenation of trans-[alpha]-Methylstilbene	p. 46
Conclusion	p. 47
References	p. 48
2.3 Synthesis and application of heterocyclic phosphine oxazoline (HetPHOX) iridium complexes for the asymmetric hydrogenation of alkenes	p. 48
2.3.1 Synthesis of (4S)-tert-Butyl-2-(thiophene-2-yl)-4,5-dihydrooxazole	p. 49
2.3.2 Synthesis of (4S)-tert-Butyl-2-(3-diphenylphosphino-thiophene-2-yl)-4,5-dihydrooxazole	p. 50
2.3.3 Synthesis of (4S)-[([eta superscript 4]-1,5-Cyclooctadiene)-{{4-tert-butyl-2-(3-diphenylphosphino-thiophene-2-yl)-4,5-dihydrooxazole}}iridium(I)]-tetrakis [3,5-bis(trifluoromethyl)phenyl]borate	p. 52
2.3.4 Asymmetric hydrogenation of trans-[alpha]-Methylstilbene	p. 53
Conclusion	p. 54
References	p. 54
2.4 (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	p. 55
2.4.1 Synthesis of 3-Bromo-2,6-dimethoxypyridine	p. 55
2.4.2 Synthesis of Bis(3,5-dimethylphenyl)phosphine chloride	p. 56
2.4.3 Synthesis of 3-Bromo-2,6-dimethoxy-4-di(3,5-dimethylphenyl)phosphinopyridine	p. 57
2.4.4 Synthesis of 3-Bromo-2,6-dimethoxy-4-di(3,5-dimethylphenyl)phosphinopyridine	p. 59
2.4.5 2,2[prime],6,6[prime]-Tetramethoxy-bis[di(3,5-dimethylphenyl)phosphinoyl]-3,3[prime]-bipyridine	p. 60
2.4.6 Optical resolution of ([plus or minus])-6 with (-) or (+)-2,3-0,0[prime]-Dibenzoyltartaric acid monohydrate [(R)-6 or (S)-6)]	p. 61
2.4.7 (R)-2,2[prime],6,6[prime]-Tetramethoxy-bis[di(3,5-dimethylphenyl)phosphino]-3,3[prime]-bipyridine [(R)-Xyl-P-Phos, (R)-1]	p. 62
2.4.8 Preparation of the stock solution of [Rh(R-Xyl-P-Phos)(COD)]BF[subscript 4]	p. 63
2.4.9 A typical procedure for the asymmetric hydrogenation of methyl (Z)-2-Acetamidocinnamate	p. 64
References	p. 65
2.5 (R,R)-2,3-Bis(tert-butylmethylphosphino)quinoxaline (QuinoXP) as a ligand for rhodium-catalyzed asymmetric hydrogenation of prochiral amino acid and amine derivatives	p. 55
2.5.1 Synthesis of (R)-tert-Butyl(hydroxymethyl)methylphosphine-borane	p. 66
2.5.2 Synthesis of (R)-Benzoyloxy(tert-butyl)methylphosphine-borane	p. 67
2.5.3 Synthesis of (S)-tert-Butylmethylphosphine-borane	p. 69
2.5.4 (R,R)-2,3-Bis(tert-butylmethylphosphino)quinoxaline (QuinoxP)	p. 70
2.5.5 Asymmetric hydrogenation of Methyl (E)-3-acetylamino-2-butenoate catalyzed by Rh(I)-(R,R)-2,3-Bis(tert-butylmethylphosphino)quinoxaline	p. 71
Conclusion	p. 72
References	p. 73
2.6 Rhodium-catalyzed asymmetric hydrogenation of indoles	p. 73
2.6.1 Synthesis of (R)-2-[(S)-1-(Dimethylamino)ethyl]-1-iodoferrocene	p. 73
2.6.2 Synthesis of (R)-2-[(S)-1-(Diphenylphosphinyl)ethyl]-1-iodoferrocene	p. 75
2.6.3 Synthesis of (R,R)-2,2[prime]-Bis[(S)-1-(diphenylphosphinyl)ethyl]-1,1[Prime]-biferrocene	p. 78
2.6.4 Synthesis of (R,R)-2,2[Prime]-Bis[(S)-1-(diphenylphosphino)ethyl]-1,1[Prime]-biferrocene [abbreviated to (S,S)-(R,R)-PhTRAP]	p. 80
2.6.5 Catalytic asymmetric hydrogenation of N-Acetyl-2-butylindole	p. 82
2.6.6 Catalytic asymmetric hydrogenation of 3-Methyl-N-(p-toluenesulfonyl)indole	p. 84
Conclusion	p. 85
References	p. 86
3 Asymmetric Reduction of Ketones	p. 87
3.1 (R,R)-Bis(diphenylphosphino)-1,3-diphenylpropane as a versatile ligand for enantioselective hydrogenations	p. 89
3.1.1 Synthesis of (S,S)-1,3-Diphenylpropane-1,3-diol	p. 89
3.1.2 Synthesis of (S,S)-Methanesulfonyloxy-1,3-diphenylpropane-1,3-diol	p. 91
3.1.3 Synthesis of (R,R)-Bis(diphenylphosphino)-1,3-diphenylpropane	p. 91
Conclusion	p. 93
References	p. 93
3.2 Synthesis of both enantiomers of 1-Phenylethanol by reduction of acetophenone with Geotrichum candidum IFO 5767	p. 93
3.2.1 Cultivation of G. candidum IFO 5767	p. 94
3.2.2 Synthesis of (S)-1-Phenylethanol	p. 95
3.2.3 Synthesis of (R)-1-Phenylethanol	p. 95
Conclusion	p. 97
References	p. 97
3.3 Titanocene-catalyzed reduction of ketones in the presence of water. A convenient procedure for the synthesis of alcohols via free-radical chemistry	p. 97
3.3.1 Titanocene-catalyzed reduction of Acetophenone in the presence of water	p. 98
3.3.2 Titanocene-catalyzed synthesis of Methyl 4-deuterio-4-phenyl-4-hydroxybutanoate	p. 99
References	p. 100
3.4 Xyl-tetraPHEMP: a highly efficient biaryl ligand in the [diphosphine RuCl[subscript 2] diamine]-catalyzed hydrogenation of simple aromatic ketones	p. 101
3.4.1 Synthesis of Tri(3,5-dimethylphenyl)phosphine oxide	p. 102
3.4.2 Synthesis of Bis(3,5-dimethylphenyl)-(2-iodo-3,5-dimethylphenyl)phosphine oxide	p. 103
3.4.3 Synthesis of rac-4,4[prime],6,6[prime]-Tetramethyl-2,2[prime]-bis[bis(3,5-dimethylphenyl)phosphinoyl]-biphenyl	p. 105
3.4.4 Synthesis of rac-4,4[prime],6,6[prime]-Tetramethyl-2,2[prime]-bis[bis(3,5-dimethylphenyl)phosphino]-biphenyl [abbreviated to (rac)-Xyl-tetraPHEMP]	p. 106
3.4.5 Synthesis of [(R)-N,N-Dimethyl(1-methyl)benzylaminato-C[superscript 2],N]-{{rac-4,4[prime],6,6[prime]-tetramethyl-2,2[prime]-bis[bis(3,5-dimethylphenyl)phosphino]-biphenyl}}-palladium(II) tetrafluoroborate and separation of the diastereomers	p. 107
3.4.6 Synthesis 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]	p. 108
3.4.7 Synthesis of [(R)-Xyl-tetraPHEMP RuCl[subscript 2] (R,R)-DPEN] and [(S)-Xyl-tetraPHEMP RuCl[subscript 2] (S,S)-DPEN]	p. 110
3.4.8 Reduction of Acetophenone using [(S)-Xyl-tetraPHEMP RuCl[subscript 2] (S,S)-DPEN] as a precatalyst	p. 111
Conclusion	p. 112
References	p. 112
3.5 N-Arenesulfonyl- and N-Alkylsulfamoyl-1,2-diphenylethylenediamine ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of activated ketones	p. 113
3.5.1 Synthesis of N-Arenesulfonyl-1,2-diphenylethylenediamines	p. 113
3.5.2 Preparation of Ru(II)-N-arenesulfonyl-1,2-diphenylethylenediamine complexes	p. 114
3.5.3 Asymmetric transfer hydrogenation of Ethyl benzoylacetate	p. 115
Conclusion	p. 116
References	p. 116
3.6 The synthesis and application of BrXuPHOS: a novel monodentate phosphorus ligand for the asymmetric hydrogenation of ketones	p. 116
3.6.1 Synthesis of (S)-BrXuPHOS	p. 117
3.6.2 Synthesis of (S,S,SS)-BrXuPHOS-Ru-DPEN	p. 119
3.6.3 General procedure of asymmetric hydrogenation of acetophenone	p. 120
Conclusion	p. 121
Acknowledgement	p. 121
References	p. 121
3.7 In Situ formation of ligand and catalyst: application in ruthenium-catalyzed enantioselective reduction of ketones	p. 121
3.7.1 Synthesis of (S)-3-Fluoro-1-phenylethanol	p. 122
Conclusion	p. 123
References	p. 124
3.8 Synphos and Difluorphos as ligands for ruthenium-catalyzed hydrogenation of alkenes and ketones	p. 125
3.8.1 Synthesis of [RuCl((S)-SYNPHOS)(p-cymene)]Cl	p. 125
3.8.2 Synthesis of [RuCl((S)-DIFLUORPHOS)(p-cymene)]Cl	p. 126
3.8.3 Synthesis of [RuI((S)-DIFLUORPHOS)(p-cymene)]I	p. 127
3.8.4 Synthesis of [NH[subscript 2]R[subscript 2]] [(RuCl(PP))[subscript 2]([Mu]-Cl)[subscript 3]] PP = SYNPHOS or DIFLUORPHOS and R = Me or Et	p. 127
3.8.5 Synthesis of [NH[subscript 2]Me[subscript 2]][RuCl-(S)-DIFLUORPHOS][subscript 2][[Mu]-Cl][subscript 3]	p. 128
3.8.6 Synthesis of in situ generated [RuBr[subscript 2]((S)-SYNPHOS)] and [RuBr[subscript 2]((S)-DIFLUORPHOS)]	p. 129
Conclusion	p. 131
References	p. 131
3.9 An arene ruthenium complex with polymerizable side chains for the synthesis of immobilized catalysts	p. 132
3.9.1 Synthesis of 2-Methyl-cyclohexa-2,5-dienecarboxylic acid 2-(2-methyl-acryloyloxy)-ethyl ester	p. 133
3.9.2 Synthesis of [[eta superscript 6]-(2-Methyl-benzoic acid 2-(2-methyl-acryloyloxy)-ethyl ester)RuCl[subscript 2]][subscript 2]	p. 134
Conclusion	p. 135
References	p. 135
3.10 Selective reduction of carbonyl group in [beta], [gamma]-unsaturated [alpha]-alpha-ketoesters by transfer hydrogenation with Ru-(p-cymene) (TsDPEN)	p. 135
3.10.1 Synthesis of Di-[Mu]-chloro-bis[chloro([eta superscript 6]-1-isopropyl-4-methyl-benzene)ruthenium(II)	p. 136
3.10.2 Synthesis of ([plus or minus])-Monotosylate-1,2-diphenyl-1,2-ethylenediamine	p. 136
3.10.3 Synthesis of Ru complex Ru(p-cymene)(TsDPEN)	p. 138
3.10.4 Ru-TsDPEN catalyzed transfer hydrogenation reaction of [beta],[gamma]-unsaturated-[alpha]-ketoesters	p. 139
Conclusion	p. 140
References	p. 141
3.11 Preparation of polymer-supported Ru-TsDPEN catalysts and their use for the enantioselective synthesis of (S)-fluoxetine	p. 141
3.11.1 Synthesis of the supported ligand 9	p. 141
3.11.2 Synthesis of ligand 17	p. 148
3.11.3 General procedure for asymmetric transfer hydrogenation	p. 150
3.11.4 Preparation of (S)-Fluoxetine hydrochloride	p. 151
Conclusion	p. 154
References	p. 154
3.12 Polymer-supported chiral sulfonamide-catalyzed reduction of [beta]-keto nitriles: a practical synthesis of (R)-Fluoxetine	p. 155
3.12.1 Synthesis of (R)-3-Amino-1-phenyl-propan-1-ol	p. 155
3.12.2 Synthesis of (R)-ethyl 3-hydroxy-3-phenylpropylcarbamate	p. 156
3.12.3 Synthesis of (R)-3-(Methylamino)-1-phenylpropan-1-ol	p. 157
3.12.4 Synthesis of (R)-Fluoxetine	p. 158
Conclusion	p. 159
References	p. 159
4 Imine Reduction and Reductive Amination	p. 161
4.1 Metal-free reduction of imines: enantioselective Bronsted acid-catalyzed transfer hydrogenation using chiral BINOL-phosphates as catalysts	p. 162
4.1.1 Synthesis of (R)-2,2[prime]-Bis-methoxymethoxy-[1,1[prime]] binaphthalene (MOM-BINOL)	p. 162
4.1.2 Synthesis of (R)-3,3[prime]-Diiodo-2,2[prime]-bis(methoxymethoxy)-1,1[prime]-binaphthalene	p. 164
4.1.3 Synthesis of 3,3[prime]-Bis-(3,5[prime]-bis-trifluoromethyl-phenyl)-2,2[prime]-bismethoxymethoxy [1,1[prime]-binaphthalene]	p. 165
4.1.4 Synthesis of (R)-3,3[prime]-[3,5-Bis(trifluoromethyl)phenyl]-1,1[prime]-binaphthylphosphate	p. 166
4.1.5 General procedure for the transfer hydrogenation of ketimines	p. 167
4.1.6 Synthesis of [1-(2,4-Dimethyl-phenyl)-ethyl]-(4-methoxy-phenyl)-amine	p. 167
Conclusion	p. 168
References	p. 170
4.2 Metal-free Bronsted acid-catalyzed transfer hydrogenation: enantioselective synthesis of tetrahydroquinolines	p. 170
4.2.1 General procedure for the transfer hydrogenation of quinolines	p. 170
4.2.2 Synthesis of 7-Chloro-4-phenyl-1,2,3,4-tetrahydroquinoline	p. 172
4.2.3 Synthesis of (S)-2-Phenyl-1,2,3,4-tetrahydroquinoline	p. 172
4.2.4 Synthesis of (R)-2-(2-(Benzo[1,3]dioxol-5-yl)ethyl)-1,2.3,4-tetrahydro-quinoline	p. 173
Conclusion	p. 174
References	p. 174
4.3 A highly stereoselective synthesis of 3[alpha]-Amino-23,24-bisnor-5[alpha]-cholane via reductive amination	p. 175
4.3.1 Synthesis of Tris[(2-ethylhexanoyl)oxy]borohydride	p. 177
4.3.2 Synthesis of 3[alpha]-Acetamino-23,24-bisnor-5[alpha]-cholane	p. 177
4.3.3 Synthesis of 3[alpha]-N-1-[N(3-[4-Aminobutyl])-1,3-diaminopropane]-23,24-bisnor-5[alpha]-cholane	p. 179
Conclusion	p. 181
Acknowledgements	p. 181
References	p. 181
5 Oxidation of Primary and Secondary Alcohols	p. 183
5.1 Copper(Il) catalyzed oxidation of primary alcohols to aldehydes with atmospheric oxygen	p. 183
5.1.1 Synthesis of copper(II) complex 1	p. 184
5.1.2 Typical procedure for the oxidation of primary alcohols to aldehydes	p. 185
Conclusion	p. 186
References	p. 187
5.2 Solvent-free dehydrogenation of secondary alcohols in the absence of hydrogen abstractors using Robinson's catalyst	p. 187
5.2.1 Dehydrogenation of 2-Octanol using Ru(OCOCF[subscript 3])[subscript 2](CO)(PPh[subscript 3])[subscript 2] as a catalyst	p. 187
Conclusion	p. 188
References	p. 188
5.3 2-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	p. 188
5.3.1 Synthesis of 1-Hydroxy-5-decanone	p. 189
Conclusion	p. 192
References	p. 192
6 Hydroxylation, Epoxidation and Related Reactions	p. 193
6.1 Proline-catalyzed [alpha]-aminoxylation of aldehydes and ketones	p. 194
6.1.1 Synthesis of (R)-2-Anilinoxypropanol	p. 195
6.1.2 Synthesis of (R)-7-Anilinoxy-1,4-dioxaspiro[4.5]decan-8-one	p. 196
Conclusion	p. 197
References	p. 198
6.2 Ru/Silia Cat TEMPO-mediated oxidation of alkenes to [alpha]-hydroxyacids	p. 199
6.2.1 Synthesis of Silia Cat TEMPO	p. 199
6.2.2 Synthesis of 2-(4-Chlorophenyl)-1,2-propanediol	p. 201
6.2.3 Synthesis of 2-(4-Chlorophenyl)-1,2-hydroxypropanoic acid	p. 202
Conclusion	p. 204
References	p. 204
6.3 Catalytic enantioselective epoxidation of trans-disubstituted and trisubstituted alkenes with arabinose-derived ulose	p. 204
6.3.1 Synthesis of 2[prime],3[prime]-Diisobutyl acetal	p. 205
6.3.2 Synthesis of ulose	p. 206
6.3.3 Asymmetric epoxidation of trans-[alpha]-Methylstilbene using ulose as catalyst at 0 [degree]C	p. 208
Conclusion	p. 209
References	p. 210
6.4 VO(acac)[subscript 2]/TBHP catalyzed epoxidation of 2-(2-Alkenyl)phenols. highly regio- and diastereoselective oxidative cyclisation to 2,3-Dihydrobenzofuranols and 3-Chromanols	p. 211
6.4.1 VO(acac)[subscript 2]/TBHP catalyzed epoxidation of 2-(3,7-Dimethyl-octa-2,6-dienyl)-phenol	p. 212
6.4.2 VO(acac)[subscript 2]/TBHP/TFA catalyzed oxidative cyclization of 2-(3,7-Dimethyl-octa-2,6-dienyl)-phenol	p. 213
Conclusion	p. 214
References	p. 214
6.5 An Oxalolidinone ketone catalyst for the asymmetric epoxidation of cis-olefins	p. 215
6.5.1 Amadori rearrangement to give 1-Dibenzylamino-1-deoxy-D-fructose	p. 215
6.5.2 Acetal protection of 1-Dibenzylamino-1-deoxy-D-fructose	p. 216
6.5.3 Hydrogenation of the Dibenzylamine	p. 217
6.5.4 Phosgene cyclization of aminoalcohol	p. 218
6.5.5 Alcohol oxidation	p. 220
6.5.6 Synthesis of ketone 2	p. 221
6.5.7 Asymmetric epoxidation of cis-[beta]-Methylstyrene	p. 222
Conclusion	p. 223
References	p. 224
6.6 [alpha]-Fluorotropinone immobilised on silica: a new stereoselective heterogeneous catalyst for epoxidation of alkenes with oxone	p. 225
6.6.1 Synthesis of silica KG-60-supported enantiomerically enriched [alpha]-Fluorotropinone	p. 225
6.6.2 Synthesis of enantiomerically enriched epoxides	p. 226
Conclusion	p. 227
References	p. 228
6.7 Asymmetric epoxidation catalyzed by novel azacrown ether-type chiral quaternary ammonium salts under phase-transfer catalytic conditions	p. 228
6.7.1 Synthesis of precursor of the azacrown ether	p. 229
6.7.2 Synthesis of the azacrown ether	p. 230
6.7.3 Synthesis of the azacrown ether-type quaternary ammonium salt	p. 232
6.7.4 Asymmetric epoxidation of (E)-Chalcone catalyzed by the azacrown ether-type quaternary ammonium salt as chiral PTC	p. 233
Conclusion	p. 234
References	p. 235
6.8 Enantioselective epoxidation of olefins using phase transfer conditions and a chiral [azepinium][TRISPHAT] salt as catalyst	p. 235
6.8.1 Enantioselective epoxidation of 1-Phenyl-3,4-dihydronaphthalene	p. 236
Conclusion	p. 238
References	p. 239
6.9 Catalytic asymmetric epoxidation of [alpha],[beta]-unsaturated esters promoted by a Yttrium-biphenyldiol complex	p. 239
6.9.1 Synthesis of (aS,R)-6,6[prime]-[(Propylene)dioxy]biphenyl-2,2[prime]-diol	p. 240
6.9.2 Synthesis of (aS,R)-2,2-[Oxybis(ethylene)dioxy]-6,6[prime]-[(propylene)dioxy]biphenyl	p. 242
6.9.3 Synthesis of (S)-6,6[prime]-[Oxybis(ethylene)dioxy]biphenyl-2,2[prime]-diol	p. 243
6.9.4 Enantiomeric enrichment of (S)-6,6[prime]-[Oxybis(ethylene)dioxy]biphenyl-2,2[prime]-diol	p. 244
6.9.5 Catalytic asymmetric epoxidation of [alpha],[beta]-unsaturated esters	p. 246
References	p. 248
6.10 Catalytic enantioselective epoxidation of [alpha],[beta]-enones with a binol-zinc-complex	p. 249
6.10.1 Synthesis of (E)-(2S,3R)-Phenyl-(3-phenyloxiran-2-yl)methanone	p. 249
Conclusion	p. 250
References	p. 251
6.11 Asymmetric epoxidation of Phenyl-2-(3[prime]-pyridylvinyl)sulfone using polyleucine hydrogen peroxide gel	p. 251
6.11.1 Preparation of polyleucine-hydrogen peroxide gel	p. 252
6.11.2 Synthesis of Phenyl-2-(3[prime]-pyridylvinyl) sulfone (2)	p. 252
References	p. 254
7 Oxidation of Ketones to Lactones or Enones	p. 255
7.1 Synthesis of 2-(Phosphinophenyl)pyrindine ligand and its application to palladium-catalyzed asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones	p. 256
7.1.1 Synthesis of (7R)-2-(2-Hydroxyphenyl)-7-isopropyl-6,7-dihydro-5H-1-pyrindine	p. 256
7.1.2 2-[2-(Diphenylphosphinoyl)phenyl]-7-isopropyl-6,7-dihydro-5H-1-pyrindine	p. 258
7.1.3 2-[2-(Diphenylphosphanyl)phenyl]-7-isopropyl-6,7-dihydro-5H-1-pyrindine	p. 259
7.1.4 Asymmetric Baeyer-Villiger oxidation of 3-Phenylcyclobutanone	p. 261
Conclusion	p. 262
References	p. 263
7.2 (D)-Codeinone from (D)-Dihydrocodeinone via the use of modified o-iodoxybenzoic acid (IBX). A convenient oxidation of ketones to enones	p. 263
7.2.1 Synthesis of IBX	p. 264
7.2.2 Synthesis of codeinone	p. 264
References	p. 266
8 Oxidative C-C Coupling	p. 267
8.1 Enantioselective oxidative coupling of 2-Naphthols catalyzed by a novel chiral vanadium complex	p. 267
8.1.1 Synthesis of 3,3-Diformyl-2,2[prime]-biphenol	p. 268
8.1.2 Synthesis of chiral vanadium complexes	p. 270
8.1.3 Catalytic oxidative coupling of 7-Alkoxy-1-naphthols by chiral vanadium complexes	p. 271
Reference	p. 272
8.2 Catalytic oxidative cross-coupling reaction of 2-Naphthol derivatives	p. 273
8.2.1 Synthesis of Methyl 2,2[prime]-dihydroxy-1,1[prime]-binaphthalene-3-carboxylate	p. 273
Conclusion	p. 274
References	p. 275
8.3 Oxidative coupling of benzenes with [alpha],[beta]-unsaturated aldehydes by Pd(OAc)[subscript 2]/ HPMoV/ O[subscript 2] system	p. 275
8.3.1 Synthesis of Cinnamaldehyde	p. 276
Conclusion	p. 278
References	p. 278
9 Oxidation of Sulfides and Sulfoxides	p. 279
9.1 The first example of direct oxidation of sulfides to sulfones by an osmate-molecular oxygen system	p. 280
9.1.1 Synthesis of osmate exchanged Mg-Al layered double hydroxides (LDH-OsO[subscript 4])	p. 280
9.1.2 Synthesis of Methyl phenyl sulfone or Methylsulfonylbenzene	p. 281
Conclusion	p. 282
References	p. 283
9.2 Selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide in the presence of zirconium tetrachloride	p. 283
9.2.1 Oxidation of Benzyl 4-bromobenzyl sulfide to Benzyl 4-bromobenzyl sulfoxide using H[subscript 2]O[subscript 2] in the presence of zirconium tetrachloride	p. 284
9.2.2 Oxidation of Benzyl 4-bromobenzyl sulfide to Benzyl 4-bromobenzyl sulfone using H[subscript 2]O[subscript 2] in the presence of zirconium tetrachloride	p. 286
Conclusion	p. 287
References	p. 287
9.3 WO[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	p. 288
9.3.1 Synthesis of (R)-2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimadazole {{(R)-(+)-Lansoprazole}}	p. 288
9.3.2 Synthesis of (R)-(+)-Phenyl benzyl sulfoxide	p. 290
Conclusion	p. 293
References	p. 293
9.4 Benzyl-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	p. 293
9.4.1 Synthesis of Benzyl-4,6-O-isopropylidene-[alpha]-D-glucopyranoside, 2-deoxy-2-[[(2-hydroxy-3,5-di-tert-butylphenyl)methylene]imine]	p. 294
9.4.2 Oxidation of Thioanisole	p. 295
Conclusion	p. 296
References	p. 296
9.5 Asymmetric sulfoxidation of aryl methyl sulfides with hydrogen peroxide in water	p. 297
9.5.1 Synthesis of complex (R)-BINAP)PtCl[subscript 2]	p. 298
9.5.2 Synthesis of complex [((R)-BINAP)Pt((OH)][subscript 2](BF[subscript 4])[subscript 2]	p. 299
9.5.3 Stereoselective catalytic oxidation of aryl methyl sulfides	p. 300
Conclusion	p. 300
References	p. 301
Index	p. 303