Page 1335 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1312 Ketones (Cont.) boranes, 787–792
aryl carboxylate salts and organolithium
Index reduction by silanes, 427 compounds, 644–645
synthesis by Friedel-Crafts acylation, carboxylic acid derivatives by Pd-catalyzed
1017–1023 coupling, 736, 743, 747–748
carboxylation of, 154 epoxides by rearrangement, 1111–1114
cyclic hydrazones by alkylation, 52–53
ring expansion with diazo compounds, imines by alkylation, 51–54
891–893 -keto esters by alkylation, 23–24
stereoselective reduction of, 407–410 N-methoxy-N-methyl carboxamides and
synthesis by hydrocarbonylation, 749 organolithium compounds, 638
-diazo nitriles and organomagnesium compounds,
esters from by Wolff rearrangement, 941–944 637
metal carbenes from, 926–930 organotin compounds by Pd-catalyzed
synthesis, 910–912 carbonylation, 752
enolates pyridine-2-thiol esters and organomagnesium
acylation of, 155–156 compounds, 638
aldol reactions, 67–71 , -unsaturated
alkylation of, 24–31 conjugate addition reactions of, 184, 189,
oxidation by oxaziridines, 1141 686–696, 830–833
fluorination, 331 enolates of, 12, 30–31
-halo from Mannich bases, 140–142
Favorskii rearrangement of, 892–895 organocopper addition, 686–696
reactions with organoboranes, 792 photocycloaddition reactions, 544–549
-halogenation, 328–331 reduction by lithium metal, 436
hydrogenation synthesis from
enantioselective, 391–395 alkenyl mercury compounds, 663
-hydroxymethylene derivatives, 155 silanes, 828–829
methyl stannanes, 754
oxidation by hypochlorite, 329 1,2- versus 1,4-reduction, 406–407, 419
-oxy , -unsaturated
reductive deoxygenation, 441–443 from acylation of allyl silanes, 829
organocerium compounds, reaction with, , -unsaturated
665–666 from Claisen rearrangement, 561–564
organomagnesium compounds, reactions with zinc enolates, reaction with, 657–660
alcohols from, 637–638 Khmds, see Potassium hexamethyldisilazide
chelation effect in, 649 Knoevenagel reactions, 147–148
enantioselective catalyst for, 649 decarboxylation during, 147
enolization during, 642 examples, 148
reduction during, 642 K-Selectride®, see potassium tris-(1-methylpropyl)
stereochemistry of, 648 borohydride
oxidation, 1131–1143
Baeyer-Villiger, 1134–1138
dicarboxylic acids from cyclic, 1131 Lactate esters as chiral auxiliaries for
oxaziridines, 1141 Diels-Alder reaction, 499–501
selenium dioxide, 1143 Lactones
reaction with dithiolane derivatives of, 276
azides, lactams from, 951 iodo, by iodolactonization, 312–316
hydrazoic acid, amides from, 950 -methylene, synthesis of, 142
reduction of, 407–415 partial reduction by DiBAlH, 401
enantioselective, 415–421 synthesis
chelation control in, 411–415 from ethers by oxidation, 1069
synthesis from macrocyclic, 248–249
acyl chlorides, 637, 657, 662–663, 739–743 Lanthanide, organo- compounds, 664–666
alcohols by oxidation, 1063–1074 Lanthanide salts
alkenes by hydroboration-oxidation, 345 alkoxides, as hydride transfer catalysts, 429
alkenes by Pd-catalyzed oxidation, 709–712 as catalysts for
alkynes by mercury-catalyzed hydration, aromatic nitration, 1004
335–6 carbonyl ene reaction, 874–875