Regio- and Stereo-Controlled Oxidations and Reductions, Volume 5

by Roberts, Stanley M.; Whittall, John

Edition: 1st

ISBN13: 9780470090220

ISBN10: 0470090227

Format: Hardcover

Pub. Date: 2007-09-11

Publisher(s): Wiley-Interscience

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Summary

Volume 5 in the Catalysts for Fine Chemical Synthesis series describes new procedures for the regio- and stereo-controlled transformations of compounds involving oxidation or reduction reactions. It describes a wide range of catalysts, including organometallic systems, biocatalysts and biomimetics. This volume also includes descriptions of a variety of conversions, including: Baeyer-Villiger oxidations; Epoxidation reactions; Hydroxylation reactions; Oxidation of alcohols to aldehydes, ketones and carboxylic acids; Reduction of ketones; and Reduction of alkenes including Î±, Î²-unsaturated carbonyl compounds. The book will be an important text for practising synthetic organic chemists in industry and academia. Protocols are written in a standard format by the authors who have discovered them Hints, tips and safety advice (where appropriate) is given to ensure that the procedures are reproducible Indications are given as to the range of starting materials used and, where appropriate, comparisons to alternative methodology Includes relevant references to the primary literature.

Author Biography

Stanley M. Roberts is the editor of Regio- and Stereo-Controlled Oxidations and Reductions, Volume 5, published by Wiley. John Whittall is the editor of Regio- and Stereo-Controlled Oxidations and Reductions, Volume 5, published by Wiley.

Series Preface	p. xvii
Preface to Volume 5	p. xix
Abbreviations	p. xxi
Industrial Catalysts for Regio- or Stereo-Selective Oxidations and Reductions A Review of Key Technologies and Targets	p. 1
Introduction	p. 2
Reduction of Carbon-Carbon Double Bonds	p. 3
Privileged structures: [alpha]-amino acids and itaconic acids	p. 4
[beta]-Amino acids	p. 5
[alpha]-Alkyl substituted acids	p. 6
[alpha]-Alkoxy substituted acids	p. 8
Unsaturated nitriles	p. 9
Alkenes and allyl alcohols	p. 10
[alpha],[beta]-Unsaturated aldehyde reduction	p. 10
Ketone and Imine Reduction	p. 12
Catalytic hydrogenation of ketones and imines	p. 12
Asymmetric transfer hydrogenation (ATH) catalysts	p. 15
Modified borane reagents	p. 20
Biocatalysts (alcohol dehydrogenases and ketoreductases)	p. 21
Oxidation	p. 23
Sharpless chiral epoxidation of allyl alcohols	p. 23
Dioxirane catalyzed epoxidation	p. 23
Amines and iminium salts	p. 25
Phase transfer catalysts	p. 25
The Julia-Colonna method (polyleucine oxidation)	p. 26
Organocatalytic [alpha]-hydroxylation of ketones	p. 27
Baeyer-Villiger oxidation	p. 27
Chiral sulfoxides	p. 28
References	p. 29
Asymmetric Hydrogenation of Alkenes, Enones, Ene-Esters and Ene-Acids	p. 35
(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
Synthesis of (S)-5,5[prime],6,6[prime],7,7[prime],8,8[prime]-Octahydro-1,1[prime]-bi-2-naphthol	p. 37
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
Asymmetric hydrogenation of Dimethyl itaconate	p. 40
Conclusion	p. 41
References	p. 41
Synthesis and application of phosphinite oxazoline iridium complexes for the asymmetric hydrogenation of alkenes	p. 42
Synthesis of (4S,5S)-2-(5-Methyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-1,3-diphenyl-propan-2-ol	p. 42
Synthesis of (4S,5S)-O-[1-Benzyl-1-(5-methyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-2-phenyl-ethyl]-diphenylphosphinite	p. 43
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
Asymmetric hydrogenation of trans-[alpha]-Methylstilbene	p. 46
Conclusion	p. 47
References	p. 48
Synthesis and application of heterocyclic phosphine oxazoline (HetPHOX) iridium complexes for the asymmetric hydrogenation of alkenes	p. 48
Synthesis of (4S)-tert-Butyl-2-(thiophene-2-yl)-4,5-dihydrooxazole	p. 49
Synthesis of (4S)-tert-Butyl-2-(3-diphenylphosphino-thiophene-2-yl)-4,5-dihydrooxazole	p. 50
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
Asymmetric hydrogenation of trans-[alpha]-Methylstilbene	p. 53
Conclusion	p. 54
References	p. 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	p. 55
Synthesis of 3-Bromo-2,6-dimethoxypyridine	p. 55
Synthesis of Bis(3,5-dimethylphenyl)phosphine chloride	p. 56
Synthesis of 3-Bromo-2,6-dimethoxy-4-di(3,5-dimethylphenyl)phosphinopyridine	p. 57
Synthesis of 3-Bromo-2,6-dimethoxy-4-di(3,5-dimethylphenyl)phosphinopyridine	p. 59
2,2[prime],6,6[prime]-Tetramethoxy-bis[di(3,5-dimethylphenyl)phosphinoyl]-3,3[prime]-bipyridine	p. 60
Optical resolution of ([plus or minus])-6 with (-) or (+)-2,3-0,0[prime]-Dibenzoyltartaric acid monohydrate [(R)-6 or (S)-6)]	p. 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]	p. 62
Preparation of the stock solution of [Rh(R-Xyl-P-Phos)(COD)]BF[subscript 4]	p. 63
A typical procedure for the asymmetric hydrogenation of methyl (Z)-2-Acetamidocinnamate	p. 64
References	p. 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	p. 55
Synthesis of (R)-tert-Butyl(hydroxymethyl)methylphosphine-borane	p. 66
Synthesis of (R)-Benzoyloxy(tert-butyl)methylphosphine-borane	p. 67
Synthesis of (S)-tert-Butylmethylphosphine-borane	p. 69
(R,R)-2,3-Bis(tert-butylmethylphosphino)quinoxaline (QuinoxP)	p. 70
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
Rhodium-catalyzed asymmetric hydrogenation of indoles	p. 73
Synthesis of (R)-2-[(S)-1-(Dimethylamino)ethyl]-1-iodoferrocene	p. 73
Synthesis of (R)-2-[(S)-1-(Diphenylphosphinyl)ethyl]-1-iodoferrocene	p. 75
Synthesis of (R,R)-2,2[prime]-Bis[(S)-1-(diphenylphosphinyl)ethyl]-1,1[Prime]-biferrocene	p. 78
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
Catalytic asymmetric hydrogenation of N-Acetyl-2-butylindole	p. 82
Catalytic asymmetric hydrogenation of 3-Methyl-N-(p-toluenesulfonyl)indole	p. 84
Conclusion	p. 85
References	p. 86
Asymmetric Reduction of Ketones	p. 87
(R,R)-Bis(diphenylphosphino)-1,3-diphenylpropane as a versatile ligand for enantioselective hydrogenations	p. 89
Synthesis of (S,S)-1,3-Diphenylpropane-1,3-diol	p. 89
Synthesis of (S,S)-Methanesulfonyloxy-1,3-diphenylpropane-1,3-diol	p. 91
Synthesis of (R,R)-Bis(diphenylphosphino)-1,3-diphenylpropane	p. 91
Conclusion	p. 93
References	p. 93
Synthesis of both enantiomers of 1-Phenylethanol by reduction of acetophenone with Geotrichum candidum IFO 5767	p. 93
Cultivation of G. candidum IFO 5767	p. 94
Synthesis of (S)-1-Phenylethanol	p. 95
Synthesis of (R)-1-Phenylethanol	p. 95
Conclusion	p. 97
References	p. 97
Titanocene-catalyzed reduction of ketones in the presence of water. A convenient procedure for the synthesis of alcohols via free-radical chemistry	p. 97
Titanocene-catalyzed reduction of Acetophenone in the presence of water	p. 98
Titanocene-catalyzed synthesis of Methyl 4-deuterio-4-phenyl-4-hydroxybutanoate	p. 99
References	p. 100
Xyl-tetraPHEMP: a highly efficient biaryl ligand in the [diphosphine RuCl[subscript 2] diamine]-catalyzed hydrogenation of simple aromatic ketones	p. 101
Synthesis of Tri(3,5-dimethylphenyl)phosphine oxide	p. 102
Synthesis of Bis(3,5-dimethylphenyl)-(2-iodo-3,5-dimethylphenyl)phosphine oxide	p. 103
Synthesis of rac-4,4[prime],6,6[prime]-Tetramethyl-2,2[prime]-bis[bis(3,5-dimethylphenyl)phosphinoyl]-biphenyl	p. 105
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
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
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
Synthesis of [(R)-Xyl-tetraPHEMP RuCl[subscript 2] (R,R)-DPEN] and [(S)-Xyl-tetraPHEMP RuCl[subscript 2] (S,S)-DPEN]	p. 110
Reduction of Acetophenone using [(S)-Xyl-tetraPHEMP RuCl[subscript 2] (S,S)-DPEN] as a precatalyst	p. 111
Conclusion	p. 112
References	p. 112
N-Arenesulfonyl- and N-Alkylsulfamoyl-1,2-diphenylethylenediamine ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of activated ketones	p. 113
Synthesis of N-Arenesulfonyl-1,2-diphenylethylenediamines	p. 113
Preparation of Ru(II)-N-arenesulfonyl-1,2-diphenylethylenediamine complexes	p. 114
Asymmetric transfer hydrogenation of Ethyl benzoylacetate	p. 115
Conclusion	p. 116
References	p. 116
The synthesis and application of BrXuPHOS: a novel monodentate phosphorus ligand for the asymmetric hydrogenation of ketones	p. 116
Synthesis of (S)-BrXuPHOS	p. 117
Synthesis of (S,S,SS)-BrXuPHOS-Ru-DPEN	p. 119
General procedure of asymmetric hydrogenation of acetophenone	p. 120
Conclusion	p. 121
Acknowledgement	p. 121
References	p. 121
In Situ formation of ligand and catalyst: application in ruthenium-catalyzed enantioselective reduction of ketones	p. 121
Synthesis of (S)-3-Fluoro-1-phenylethanol	p. 122
Conclusion	p. 123
References	p. 124
Synphos and Difluorphos as ligands for ruthenium-catalyzed hydrogenation of alkenes and ketones	p. 125
Synthesis of [RuCl((S)-SYNPHOS)(p-cymene)]Cl	p. 125
Synthesis of [RuCl((S)-DIFLUORPHOS)(p-cymene)]Cl	p. 126
Synthesis of [RuI((S)-DIFLUORPHOS)(p-cymene)]I	p. 127
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
Synthesis of [NH[subscript 2]Me[subscript 2]][RuCl-(S)-DIFLUORPHOS][subscript 2][[Mu]-Cl][subscript 3]	p. 128
Synthesis of in situ generated [RuBr[subscript 2]((S)-SYNPHOS)] and [RuBr[subscript 2]((S)-DIFLUORPHOS)]	p. 129
Conclusion	p. 131
References	p. 131
An arene ruthenium complex with polymerizable side chains for the synthesis of immobilized catalysts	p. 132
Synthesis of 2-Methyl-cyclohexa-2,5-dienecarboxylic acid 2-(2-methyl-acryloyloxy)-ethyl ester	p. 133
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
Selective reduction of carbonyl group in [beta], [gamma]-unsaturated [alpha]-alpha-ketoesters by transfer hydrogenation with Ru-(p-cymene) (TsDPEN)	p. 135
Synthesis of Di-[Mu]-chloro-bis[chloro([eta superscript 6]-1-isopropyl-4-methyl-benzene)ruthenium(II)	p. 136
Synthesis of ([plus or minus])-Monotosylate-1,2-diphenyl-1,2-ethylenediamine	p. 136
Synthesis of Ru complex Ru(p-cymene)(TsDPEN)	p. 138
Ru-TsDPEN catalyzed transfer hydrogenation reaction of [beta],[gamma]-unsaturated-[alpha]-ketoesters	p. 139
Conclusion	p. 140
References	p. 141
Preparation of polymer-supported Ru-TsDPEN catalysts and their use for the enantioselective synthesis of (S)-fluoxetine	p. 141
Synthesis of the supported ligand 9	p. 141
Synthesis of ligand 17	p. 148
General procedure for asymmetric transfer hydrogenation	p. 150
Preparation of (S)-Fluoxetine hydrochloride	p. 151
Conclusion	p. 154
References	p. 154
Polymer-supported chiral sulfonamide-catalyzed reduction of [beta]-keto nitriles: a practical synthesis of (R)-Fluoxetine	p. 155
Synthesis of (R)-3-Amino-1-phenyl-propan-1-ol	p. 155
Synthesis of (R)-ethyl 3-hydroxy-3-phenylpropylcarbamate	p. 156
Synthesis of (R)-3-(Methylamino)-1-phenylpropan-1-ol	p. 157
Synthesis of (R)-Fluoxetine	p. 158
Conclusion	p. 159
References	p. 159
Imine Reduction and Reductive Amination	p. 161
Metal-free reduction of imines: enantioselective Bronsted acid-catalyzed transfer hydrogenation using chiral BINOL-phosphates as catalysts	p. 162
Synthesis of (R)-2,2[prime]-Bis-methoxymethoxy-[1,1[prime]] binaphthalene (MOM-BINOL)	p. 162
Synthesis of (R)-3,3[prime]-Diiodo-2,2[prime]-bis(methoxymethoxy)-1,1[prime]-binaphthalene	p. 164
Synthesis of 3,3[prime]-Bis-(3,5[prime]-bis-trifluoromethyl-phenyl)-2,2[prime]-bismethoxymethoxy [1,1[prime]-binaphthalene]	p. 165
Synthesis of (R)-3,3[prime]-[3,5-Bis(trifluoromethyl)phenyl]-1,1[prime]-binaphthylphosphate	p. 166
General procedure for the transfer hydrogenation of ketimines	p. 167
Synthesis of [1-(2,4-Dimethyl-phenyl)-ethyl]-(4-methoxy-phenyl)-amine	p. 167
Conclusion	p. 168
References	p. 170
Metal-free Bronsted acid-catalyzed transfer hydrogenation: enantioselective synthesis of tetrahydroquinolines	p. 170
General procedure for the transfer hydrogenation of quinolines	p. 170
Synthesis of 7-Chloro-4-phenyl-1,2,3,4-tetrahydroquinoline	p. 172
Synthesis of (S)-2-Phenyl-1,2,3,4-tetrahydroquinoline	p. 172
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
A highly stereoselective synthesis of 3[alpha]-Amino-23,24-bisnor-5[alpha]-cholane via reductive amination	p. 175
Synthesis of Tris[(2-ethylhexanoyl)oxy]borohydride	p. 177
Synthesis of 3[alpha]-Acetamino-23,24-bisnor-5[alpha]-cholane	p. 177
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
Oxidation of Primary and Secondary Alcohols	p. 183
Copper(Il) catalyzed oxidation of primary alcohols to aldehydes with atmospheric oxygen	p. 183
Synthesis of copper(II) complex 1	p. 184
Typical procedure for the oxidation of primary alcohols to aldehydes	p. 185
Conclusion	p. 186
References	p. 187
Solvent-free dehydrogenation of secondary alcohols in the absence of hydrogen abstractors using Robinson's catalyst	p. 187
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
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
Synthesis of 1-Hydroxy-5-decanone	p. 189
Conclusion	p. 192
References	p. 192
Hydroxylation, Epoxidation and Related Reactions	p. 193
Proline-catalyzed [alpha]-aminoxylation of aldehydes and ketones	p. 194
Synthesis of (R)-2-Anilinoxypropanol	p. 195
Synthesis of (R)-7-Anilinoxy-1,4-dioxaspiro[4.5]decan-8-one	p. 196
Conclusion	p. 197
References	p. 198
Ru/Silia Cat TEMPO-mediated oxidation of alkenes to [alpha]-hydroxyacids	p. 199
Synthesis of Silia Cat TEMPO	p. 199
Synthesis of 2-(4-Chlorophenyl)-1,2-propanediol	p. 201
Synthesis of 2-(4-Chlorophenyl)-1,2-hydroxypropanoic acid	p. 202
Conclusion	p. 204
References	p. 204
Catalytic enantioselective epoxidation of trans-disubstituted and trisubstituted alkenes with arabinose-derived ulose	p. 204
Synthesis of 2[prime],3[prime]-Diisobutyl acetal	p. 205
Synthesis of ulose	p. 206
Asymmetric epoxidation of trans-[alpha]-Methylstilbene using ulose as catalyst at 0 [degree]C	p. 208
Conclusion	p. 209
References	p. 210
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
VO(acac)[subscript 2]/TBHP catalyzed epoxidation of 2-(3,7-Dimethyl-octa-2,6-dienyl)-phenol	p. 212
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
An Oxalolidinone ketone catalyst for the asymmetric epoxidation of cis-olefins	p. 215
Amadori rearrangement to give 1-Dibenzylamino-1-deoxy-D-fructose	p. 215
Acetal protection of 1-Dibenzylamino-1-deoxy-D-fructose	p. 216
Hydrogenation of the Dibenzylamine	p. 217
Phosgene cyclization of aminoalcohol	p. 218
Alcohol oxidation	p. 220
Synthesis of ketone 2	p. 221
Asymmetric epoxidation of cis-[beta]-Methylstyrene	p. 222
Conclusion	p. 223
References	p. 224
[alpha]-Fluorotropinone immobilised on silica: a new stereoselective heterogeneous catalyst for epoxidation of alkenes with oxone	p. 225
Synthesis of silica KG-60-supported enantiomerically enriched [alpha]-Fluorotropinone	p. 225
Synthesis of enantiomerically enriched epoxides	p. 226
Conclusion	p. 227
References	p. 228
Asymmetric epoxidation catalyzed by novel azacrown ether-type chiral quaternary ammonium salts under phase-transfer catalytic conditions	p. 228
Synthesis of precursor of the azacrown ether	p. 229
Synthesis of the azacrown ether	p. 230
Synthesis of the azacrown ether-type quaternary ammonium salt	p. 232
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
Enantioselective epoxidation of olefins using phase transfer conditions and a chiral [azepinium][TRISPHAT] salt as catalyst	p. 235
Enantioselective epoxidation of 1-Phenyl-3,4-dihydronaphthalene	p. 236
Conclusion	p. 238
References	p. 239
Catalytic asymmetric epoxidation of [alpha],[beta]-unsaturated esters promoted by a Yttrium-biphenyldiol complex	p. 239
Synthesis of (aS,R)-6,6[prime]-[(Propylene)dioxy]biphenyl-2,2[prime]-diol	p. 240
Synthesis of (aS,R)-2,2-[Oxybis(ethylene)dioxy]-6,6[prime]-[(propylene)dioxy]biphenyl	p. 242
Synthesis of (S)-6,6[prime]-[Oxybis(ethylene)dioxy]biphenyl-2,2[prime]-diol	p. 243
Enantiomeric enrichment of (S)-6,6[prime]-[Oxybis(ethylene)dioxy]biphenyl-2,2[prime]-diol	p. 244
Catalytic asymmetric epoxidation of [alpha],[beta]-unsaturated esters	p. 246
References	p. 248
Catalytic enantioselective epoxidation of [alpha],[beta]-enones with a binol-zinc-complex	p. 249
Synthesis of (E)-(2S,3R)-Phenyl-(3-phenyloxiran-2-yl)methanone	p. 249
Conclusion	p. 250
References	p. 251
Asymmetric epoxidation of Phenyl-2-(3[prime]-pyridylvinyl)sulfone using polyleucine hydrogen peroxide gel	p. 251
Preparation of polyleucine-hydrogen peroxide gel	p. 252
Synthesis of Phenyl-2-(3[prime]-pyridylvinyl) sulfone (2)	p. 252
References	p. 254
Oxidation of Ketones to Lactones or Enones	p. 255
Synthesis of 2-(Phosphinophenyl)pyrindine ligand and its application to palladium-catalyzed asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones	p. 256
Synthesis of (7R)-2-(2-Hydroxyphenyl)-7-isopropyl-6,7-dihydro-5H-1-pyrindine	p. 256
2-[2-(Diphenylphosphinoyl)phenyl]-7-isopropyl-6,7-dihydro-5H-1-pyrindine	p. 258
2-[2-(Diphenylphosphanyl)phenyl]-7-isopropyl-6,7-dihydro-5H-1-pyrindine	p. 259
Asymmetric Baeyer-Villiger oxidation of 3-Phenylcyclobutanone	p. 261
Conclusion	p. 262
References	p. 263
(D)-Codeinone from (D)-Dihydrocodeinone via the use of modified o-iodoxybenzoic acid (IBX). A convenient oxidation of ketones to enones	p. 263
Synthesis of IBX	p. 264
Synthesis of codeinone	p. 264
References	p. 266
Oxidative C-C Coupling	p. 267
Enantioselective oxidative coupling of 2-Naphthols catalyzed by a novel chiral vanadium complex	p. 267
Synthesis of 3,3-Diformyl-2,2[prime]-biphenol	p. 268
Synthesis of chiral vanadium complexes	p. 270
Catalytic oxidative coupling of 7-Alkoxy-1-naphthols by chiral vanadium complexes	p. 271
Reference	p. 272
Catalytic oxidative cross-coupling reaction of 2-Naphthol derivatives	p. 273
Synthesis of Methyl 2,2[prime]-dihydroxy-1,1[prime]-binaphthalene-3-carboxylate	p. 273
Conclusion	p. 274
References	p. 275
Oxidative coupling of benzenes with [alpha],[beta]-unsaturated aldehydes by Pd(OAc)[subscript 2]/ HPMoV/ O[subscript 2] system	p. 275
Synthesis of Cinnamaldehyde	p. 276
Conclusion	p. 278
References	p. 278
Oxidation of Sulfides and Sulfoxides	p. 279
The first example of direct oxidation of sulfides to sulfones by an osmate-molecular oxygen system	p. 280
Synthesis of osmate exchanged Mg-Al layered double hydroxides (LDH-OsO[subscript 4])	p. 280
Synthesis of Methyl phenyl sulfone or Methylsulfonylbenzene	p. 281
Conclusion	p. 282
References	p. 283
Selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide in the presence of zirconium tetrachloride	p. 283
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
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
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
Synthesis of (R)-2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimadazole {(R)-(+)-Lansoprazole}	p. 288
Synthesis of (R)-(+)-Phenyl benzyl sulfoxide	p. 290
Conclusion	p. 293
References	p. 293
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
Synthesis of Benzyl-4,6-O-isopropylidene-[alpha]-D-glucopyranoside, 2-deoxy-2-[[(2-hydroxy-3,5-di-tert-butylphenyl)methylene]imine]	p. 294
Oxidation of Thioanisole	p. 295
Conclusion	p. 296
References	p. 296
Asymmetric sulfoxidation of aryl methyl sulfides with hydrogen peroxide in water	p. 297
Synthesis of complex (R)-BINAP)PtCl[subscript 2]	p. 298
Synthesis of complex [((R)-BINAP)Pt((OH)][subscript 2](BF[subscript 4])[subscript 2]	p. 299
Stereoselective catalytic oxidation of aryl methyl sulfides	p. 300
Conclusion	p. 300
References	p. 301
Index	p. 303
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