Page 1325 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1302 Borane, derivatives (Cont.) BOX-catalysts, see Copper bis-oxazolines
borane, bis-(isopinocampheyl) chloro Bromides
Index as reducing agent, 415–416 alkenyl
carbonylation of, 786–792 synthesis by hydroboration-halogenation, 352
catechol synthesis by
hydroboration by, 340–341 hydrozirconation-bromination, 357
halo alkyl, synthesis by
hydroboration by, 340 hydroboration-bromination, 347
homologation of using -halo enolates, 792–793 oxidative decarboxylation, 1147
isopinocampheyl Bromination
enantioselective ketone synthesis using, alkenes, 298, 300
791–792 aromatic, 1009
hydroboration by, 350 Bromine azide, 306
pinacol Bromohydrins
hydroboration by, 340–341 synthesis of, 301–303
radicals from, 958–959 Bromonium ions
reactions of, 344–347 intermediates in alkene bromination, 298–300
amination, 347 1,3-butadiene
fragmentation, 899 1-methoxy-3-trimethylsiloxy-, as diene, 487–488
halogenation, 346 t-butoxycarbonyl
oxidation, 344–345, 958–959 amine protective group, 268
palladium catalyzed cross-coupling, 739–746 t-butyldimethylsilyl
stereoselective synthesis of alkenes using, as hydroxy protective group, 264
793–797
synthesis from
boron halides and organometallic reagents, Cadmium, organo- compounds, 661–662
784–785 reactions with acyl chlorides, 661–662
cuprates, 585 Calcium borohydride
thermal isomerization, 342–344 reducing agents, 399
1,1,2-trimethylpropyl, 338–339 Camphorsulfonamides as chiral auxiliaries for
Borinate esters, 785 aldol reaction, 123
Borinic acids, 785 Diels-Alder reactions, 502
Borohydrides, alkyl Carbamates
as reducing agents, 399–400, 409–411, 413, lithiation of, 630
415, 1110 nickel-catalyzed coupling of, 757
Boron enolates Carbanions, see also Enolates
aldol reactions of, 71–73, 117–119 nitrile, 34, 770, 1167
chiral, 117–119 phosphonate, 164–169
in discodermolide synthesis, 1036 -silyl
Boronate esters, 785 olefination reactions of, 171–174
alkenyl, stereospecific synthesis of alkenes stabilization by functional groups, 2–4
using, 797 Carbenes, as reaction intermediates, 903–941
ß-allyl, enantioselective addition reactions of, alkenyl, cyclopropenes from, 941
799–801 cyclopropylidene, opening to allenes, 941
palladium-catalyzed cross-coupling, 740–743 generation of
vinyl, as dienophiles, 526 from diaziridines, 913
Boronic acids, 785 from diazo compounds, 909–913
alkenyl organomercury compounds, 915–916
intramolecular Diels-Alder reactions, 526 polyhalo methanes, 914–915
palladium-catalyzed cross-coupling, 740–742 sulfonyl hydrazones, 913
aryl insertion reactions, 934–938
nickel-catalyzed cross-coupling, 758 examples, 939–940
Boron tribromide intramolecular, 938
ether cleavage by, 239 selectivity of catalyst for, 936–937
Boron trifluoride metallo-, 905, 926–929
ether cleavage by, 239 reaction with
T-BOC, see t-butoxycarbonyl alkenes, 905–908, 916–934
BOP-Cl, see Bis-(2-oxo-3-oxazoldinyl) phosphinic phenyl
chloride generation, 914–915