Page 1321 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1298 Alcohols (Cont.) alkenes by oxymercuration-reduction,
from sulfoxides by [2,3]-sigmatropic 294–298
Index rearrangement, 581 boranes by carbonylation, 786–787
by wittig reaction, 162 epoxides by reduction, 1109–1110
-amino, from epoxides, 1107 esters and organomagnesium compounds, 637
-azido, from epoxides, 1107 ketones and organometallic reagents, 638
conversion to halides, 217–223 ketones by reduction, 407–422
examples, 221 unsaturated
triphenylphosphine as co-reagent in, halocyclization of, 317–318
219–221 Aldehydes
conversion to ethers, 227 aldol reactions of, 65–78
converson to sulfonate esters, 216 aromatic
-cyano, from epoxides, 1106–1107 reduction by silanes, 425
enantioselective synthesis synthesis by formylation, 1024
by hydroboration-oxidation, 351 enolates, alkylation of, 31
by reduction of ketones, 415–422 oxidation
inversion of configuration by Mitsunobu manganese dioxide, 1132
reaction, 228 reactions with
alkynyl boranes, 805
oxidation 1063–1074
allylic boron compounds, 797–809
chromium dioxide, 1068
allylic silanes, 815–827
chromium (VI) reagents, 1063–1069
allenyl tin compounds, 850–851
Dess-Martin reagent, 1072–1073
allylic tin compounds, 834–849
dimethyl sulfoxide, 1070–1072
organomagnesium compounds, 638
manganese dioxide, 1067–1068, 1069
organozinc reagents, 653–654
oxoammonium ions, 1074
silanes from, 836
potassium ferrate, 1068
stereoselectivity of, in aldol reactions, 86–101
Swern, 1070
synthesis from
protective groups for, 258–267
alcohols by oxidation, 1063–1073
acetals as, 258–262
alkenes by hydroformylation, 759–760
allyl, 264
boranes by carbonylation, 786–787
allyloxycarbonyl, 267
formamides and organomagnesium
benzyl, 262–263
reagents, 638
t-butyl, 262
nitriles by partial reduction, 402–403
t-butyldimethylsilyl, 264
esters, by partial reduction, 401–403
dimethoxybenzyl, 263
N-methoxy-N-methylamides, 402
2,4-dimethoxytriphenylmethyl, 262
triethyl orthoformate and organomagnesium
ethers as, 262–264
reagents, 638–639
1-ethoxyethyl, 260
Alder rule, 478
2-methoxyethoxymethyl, 260
Aldol reaction
2-methoxypropyl, 259–260
of N-acylthiazoline-2-thiones, 81
methoxymethyl, 260
boron enolates in, 71–73
p-methoxyphenyl, 263
chiral, 117–119
p-methoxytrimphenylmethyl, 262 chiral auxiliaries for, 114–119
methylthiomethyl, 260 chiral catalysts for, 125–133
table of, 267 cyclic transition structure for, 67–68
tetrahydropyranyl, 260 directed 65–67
trichloroethyloxycarbonyl, 265 examples, 66
triisopropylsilyl, 264–265 double stereodifferentiation in, 108–114
trimethylsilyl, 264 examples, 111–114
2-trimethylsilylethoxymethyl, 261 enantioselective catalysts for, 125–133
triphenylmethyl, 262 examples, 133
triphenylsilyl, 265 enolate equivalents in, 65, 82–86
reductive deoxygenation via thiono esters, 433 ester enolates in, 78–81
examples, 434 generalized 64–65
synthesis from intramolecular, 134–139
aldehydes and organometallic reagents, 638 examples, 135–136
alkenes by hydroboration-oxidation, in longifolene sysnthesis, 1189
344–347, 351 Robinson annulation as, 134–139