Page 1336 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Fries rearrangement, 1023 Lithium tris-(1,2-dimethylpropyl) borohydride 1313
Mukaiyama aldol reaction, 82 as reducing agent, 399–400
LDA, see lithium di-isopropylamide Lithium tris-(1-methylpropyl) borohydride Index
Lead tetraacetate as oxidant as reducing agent, 399–400
amide oxidation, 949 Lombardo reagent, 661
diol cleavage, 1144–1145 Longifolene, multistep synthesis, 1186–1196
oxidative decarboxylation, 1145–1148 carbocation cyclization in, 1193
Lewis acid catalysis in enone photocycloaddition in, 1192
alcohol acylation, 245–246 fragmentation reaction in, 1189
carbonyl ene reaction, 869, 874 from Wieland-Miesher ketone, 1187–1190
L-Selectride®, see lithium tris-(1-methylpropyl)
Claisen rearrangement, 562
borohydride
conjugate addition of allylic silanes, 830–831
LS-Selectride®, see lithium
control of stereochemistry in aldol reaction,
tris-(1,2-dimethylpropyl) borohydride
119–125
Luche reagent, 406, 410
Diels-Alder reactions, 481–487
1,3-dipolar cycloaddition, 535–538
epoxide ring opening, 1106 MABR, see bis-(4-bromo-2,6-di-t-butylphenoxy)
Friedel-Crafts acylation, 1017 methylaluminum
Friedel-Crafts alkylation, 1014–1017 Macrocyclization by
hydrosilation, 809–811 aldol addition in epothilone a synthesis, 1224
Mukaiyama aldol reaction, 82–88, 93–95 alkene acylation, 881
organocopper reactions, 702 Curtius Rearrangement, 948
organotin reactions with carbonyl compounds, Dieckmann condensation, 149
837–838 nickel-catalyzed coupling of allylic halides, 755
rearrangement of epoxides to carbonyl olefin metathesis, 761
compounds, 1111–1112 palladium-catalyzed
Linear sequence in multistep syntheses, 1163 alkylation, 713
Lithium aluminum hydride cross-coupling of stannanes, 733–737
as reducing agent, 396–399 reductive coupling of carbonyl compounds, 444
for alkyl halides, 425 Wadsworth-Emmons reaction, 166
for epoxides, 424 Macrolactonization
Lithium borohydride by DCCI and DMAP, 249
as reducing agent, 399 by 2-imidazoly disulfide, 248
Lithium di-isopropylamide by 2-pyridyl disulfide, 248
base for enolate formation, 5, 31 by Yamaguchi method, 249
in epothilone A synthesis, 1121
Lithium hexamethyldisilazide (LiHMDS)
Magnesium, organo- compounds
base for enolate formation, 5
copper-catalyzed conjugate addition of, 690–694
Lithium tetramethylpiperidide (LiTMP)
examples, 693
base for enolate formation, 4, 69–70
mechanism, 693
Lithium b-isopinocampheyl-9-borabicyclo[3.3.1]
cross-coupling
nonane hydride
cobalt-catalyzed, 761
as enantioselective reducing agent, 415
nickel-catalyzed, 756–758
Lithium, organo- compounds
palladium-catalyzed, 724–728
alkenyl, from sulfonylhydrazones, 454–456
preparation of, 620–623
preparation of, 624–634
reaction, 634–644
by halogen-metal exchange, 632–633
acyl chlorides, 637–638
by lithiation, 627–633
carbon dioxide, 638
from sulfides, 625 carbonyl compounds, 637–444
reactions with esters, 637
carbonyl compounds, 637–645 formamides, 638
carboxylate salts, 648 halides, 636
halides, 634–637 ketones, chelation effects in, 649
N-methoxy-N-methyl carboxamides, 638 ketones, enantioselective catalysts for, 649
, -unsaturated ketones, 644 ketones, reduction during, 642
structure of, 626 ketones, stereochemistry of, 648
synthesis using, 619–620, 644–648 N-methoxy-N-methyl carboxamides, 638
examples, 646–647 nitriles, 637