Page 1327 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1304 Cerium, organo- compounds Combinatorial synthesis, 1252–1259
reactions with epothilone analogs by, 1257–1259
Index amides, 666 sample splitting method for, 1253–1254
carboxylate salts, 666 spirooxindoles by, 1256–1257
ketones, 664–666 structural diversity from, 1253
Chelation effects in tagging protocol for, 1254–1255
aldol addition reactions, 109 Ugi multicomponent reactin in, 1256
allyl silane addition reactions, 818–819 Concerted pericyclic reactions, definition, 473
allyl tin addition reactions, 838, 840 Conjugate addition
enolate alkylation, 28–29 allylic silanes, 830–833
enolate formation, 11–12 by carbon nucleophiles, 183–199
ester enolates, 80, 571 examples, 185
imine anions, 51–52 competition with 1,2-addition, 184, 189
ketone-organomagnesium reactions, 649 cyanide ion in, 198–199
Mukaiyama aldol reaction, 98 definition, 64
Cheletropic elimination, 591–593 enamines, 193
bicyclo[2.2.1]heta-2,5-dien-7-ones, 593 enantioselective catalysts for, 195–196
sulfolene dioxides, 591–592 enolate equivalents for, 190–193
Chiral auxiliaries examples, 194
for aldol reactions, 114–121 kinetic control of 186
examples, 120 of nitroalkenes, 188, 192, 198
oxazolidinones as, 114–116 organocopper compounds in, 686–694
oxazolidinone-2-thiones, 114–125 enatioselective, 702–703
thiazolidine-2-thiones, 119 organocopper-zinc reagents, 694–697
for Diels-Alder reaction, 499–504 enantioselective, 703
camphorsulfonamides as, 502 of organometallic reagents, 197–198,
examples, 503 686–695
lactate esters as, 499–501 stereoselectivity, 188, 193–197
mandelate esters as, 501 sulfur ylides and enones, 178
oxazolidinones as, 501–502 with tandem alkylation, 189–190, 690–691
pantolactone as, 500–501 Convergent steps in multistep synthesis, 1163
8-phenylmenthol as, 500 Cope elimination, see amine oxides, thermal
for enolate alkylation, 41–45 elimination
examples, 43–44 Cope rearrangement, 552–560
in discodermolide synthesis, 1236 boat versus chair transition structure for,
in Prelog-Djerassi lactone synthesis, 1205–1208 554–555, 557
Chlorination catalysis by Pd (II) salts, 555
alkynes, 335–336 examples, 558–559
aromatic, 1008–1014 oxy-Cope rearrangement, 556–557
alkenes, 300–301 examples, 559–560
Chloromethylation siloxy-Cope rearrangement, 556–557
aromatic, 1023 stereochemistry of, 552–554
Chromium, organo-compounds Copper salts as catalysts for
aromatic compound, tricarbonyl complexes, alkene photoaddition, 544–545
768–770 aromatic substitution, 1030, 1042–1045
reactions with carbanions, 770 aryl halide coupling, 703–705
Chromium oxidants carbene addition, 921–922
alcohols, 114 Copper, organo compounds, 675–706
alkenes boranes from, 585
allylic oxidation, 1116–117 catalysis in
Claisen condensation, 149–157 conjugate addition, 690–694
Claisen rearrangement, 560–564 cyclopropanation by diazo compounds,
catalysis by 924–925
Lewis acids, 562 aromatic substitution, 1042–1045
Pd (II) salts, 562 conjugate addition reactions of, 686–695
examples, 563 enantioselective, 702–703
Clark-Eschweiler reaction, 430–431 examples, 688–689
Clemmensen reduction, 452–453 mechanism, 687, 700–702
Collins reagent, 1053 tandem alkylation, 690