Page 1338 - Advanced Organic Chemistry Part B - Reactions & Synthesis

conversion to primary amides, 256, 404 in epothilone A synthesis, 1222 1315
partial reduction by DiBAlH, 402–403 in Prelog-Djerassi lactone synthesis, 847
reaction with mechanism, 764 Index
organomagnesium compounds, 634 Oligonucleotides, solid phase synthesis, 1245–1249
synthesis by phosphoramidite method for, 1251
metal-catalyzed substitution, 52 protecting groups in, 1251
nucleophilic substitution, 223–225 Oppenauer oxidation, 429
Nitrite esters, alkoxy radicals from, 991–992 Orthoester
Nitroalkanes carboxylic acid protecting group, 275–276
nucleophiles in amine-catalyzed Claisen rearrangement, 564–567
condensation, 147 reaction with organomagnesium compounds, 634
Nitroalkenes Osmium tetroxide
conjugate addition reactions of, 188, 193, dihydroxylation of alkenes, 1074–1077, 1080
198–199 computational model for, 1078–1079
dienophiles in Diels-Alder reactions, 494 co-oxidants for, 1076
Nitrones, dipolar cycloaddition of, 535–538 enantioselective, 1076–1078
N-nitroso anilides examples, 1079
aryl radicals from, 1053 Oxalate esters
Nitrosyl chloride, 306 acylation of enolates by, 150–155
Nitrosyl formate, 306 Oxalyl chloride
NMP, see n-methylpyrrolidinone Swern oxidation, 1070
Normant reagents, see copper, organo- synthesis of acyl chlorides, 243
N-Selectride®, see sodium tris-(1-methylpropyl) Oxaphosphetane
borohydride intermediate in wittig reaction, 157–164
Nucleophilic aromatic substitution, 1027–1041 Oxazaborolidines
addition-elimination mechanism, 1035–1037 chiral catalysts for aldol reactions, 126–128
elimination-addition mechanism, 1039–1041 chiral catalysts for ketone reduction, 416–418
metal-catalyzed, 1042–1052 computation model of, 418–419
copper, 1042–1045 Oxaziridines
examples, 1052 oxidation of enolates by, 1138–1142
palladium, 1045–1052 in synthesis of Baccatin III, 1211–1219
pyridine derivatives, 1037 in synthesis of discodermolide, 1233,
Nucleophilic substitution at substituted carbon 1236, 1241
catalysis by crown ethers, 224–227 Oxazolidinones, as chiral auxiliaries for
phase transfer catalysis in, 224–225 aldol reactions, 114–116
solvent effects on, 224–225 Diels-Alder reaction, 499–505
synthetic applications, 215–233 enolate alkylation, 36–42
azides, 231–232 palladium-catalyzed enolate arylation, 728
esters, 226–229 reactions with n-acyliminium ions, 145, 146
ethers, 226–227 Oxazolidine-2-thiones
examples of, 234–238 chiral auxiliaries in aldol reactions, 126–128
nitriles, 225–226 Oxetanes
phosphite esters, 228, 233 from [2+2]-photocycloaddition of alkenes and
phosphonate esters, 233 carbonyl compounds, 544–548
phosphonium salts, 225 Oxidation of
sulfides, 233 alcohols, 1063–1074
allylic alcohols, 10821088–1089
sulfonate esters, 228
computational model 1083–1087
mechanism, 1082–1083
Olefination reactions sharpless asymmetric, 1082
examples of generalized aldol reaction, 66, 155 stereoselectivity, 1082, 1085, 1087
Julia, 174–176 tartrate ligands for, 1082, 1084
Peterson reaction, 171–174 alkenes
Wadsworth-emmons reaction, 164–170 allylic, 1116–1119
Wittig Reaction, 157–164 dihydroxylation, 1074–1081
examples, 159–164 benzylic, 1148–1149
Olefin metathesis, 761–766 enolates, 1138–1142
catalysts for, 762, 763, 765 by oxaziridines, 1141–1142
examples, 765, 766 hydrocarbons, 1148–1150