Page 1343 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1320 Synthetic equivalents (Cont.) allylic, 784
in enolate alkylation, 24 -alkoxy, reactions with aldehydes, 842–845
Index homoenolate equivalents, 1169–1170 -alkoxy, addition reactions of, 843, 852
in multistep synthesis, 1163 reactions with carbonyl compounds, 838–847
nucleophilic acyl equivalents, 1167–1169 aryl, palladium-catalyzed cross-coupling of, 744
umpolung concept in, 1166 chiral, enantioselective addition reactions of,
843–846
halo, reactions with
Taddols, see
carbonyl compounds, 838
tetraaryl-1,3-dioxolane-4,5-dimethanols
organometallic compounds, 834
Tartaric acid derivatives
metal-metal exchange reactions of, 622
boronate esters of in allylboration, 801–802
tri-N-butyl
computational model for, 801–802 as hydrogen atom donor, 431–433
Taxol®, multistep synthesis, 1210–1220; see also in radical reactions, 956, 957–958, 961,
Baccatin III 979–980
Tetraaryl-1,3-dioxolane-4,5-dimethanols, palladium catalyzed cross-coupling 728–737
complexes as chiral catalyst for examples, 736–738
conjugate addition reactions to nitroalkenes, 198 mechanism, 731–732
1,3-dipolar cycloaddition, 535 synthesis of, 833–834, 838
Diels-Alder reaction, 512–513 alkenyl, from alkynes using boranes, 797
organomagesium addition to ketones, 649 alkenyl from alkynes, 833–834
organozinc addition to aldehydes, 650 -alkoxy, from aldehydes, 835
Tetraenes, conjugated from aldehydes, 835
synthesis from 2-en-1,4-diols by reductive from organometallic reagents, 834
elimination, 461 -siloxy, from aldehydes 834
Tetrahydropyranyl Titanium
protecting group for alcohols, 260 alkoxides in sharpless epoxidation, 1085–1088
Tetrafuran derivatives BINOLates
synthesis by halocyclization, 316, 317 chiral catalysts for aldol reactions, 127–132

N N N N −tetramethylethylenediamine enolates in aldol reation, 76–78

organolithium reagents, effect on, 627, 630–632 low-valent, reductive coupling by, 444–447
solvation of enolates, 20–21 TMEDA, see N,N,N’N’-tetramethylethylenediamine
1,2,4,5-tetrazines TMSI, see trimethylsilyl iodide
as Diels-Alder, dienes, 598 Transmetallation
Tetrazole in allyl tin addition reactions, 843
sulfones in Julia reaction, 175 in Pd-catalyzed cross-coupling, 728
Thallium, organo- compounds 1,2,4-triazines
preparation by electrophilic thallation, 1026 as Diels-Alder, dienes, 591, 592
Theyxlborane, see borane, 1,1,2-trimethylpropyl Trichloroethyloxycarbonyl
THF, see Tetrahydrofuran amine protective group, 266
Thioamides Trifluoroacetic acid
[3,3]-sigmatropic rearrangement of, 577, 578 addition to alkenes, 294
THP, see Tetrahydropyranyl Trifluoromethane sulfonate esters
1,3-thiazoline-2-thiones, as chiral auxiliaries alkenyl
aldol reactions of, 82, 114 reductive deoxygenation, 441
reactions with n-acyliminium ions, 145, 146 palladium-catalyzed carbonylation, 753
Thiocyanogen, 305 palladium-catalyzed cross-coupling, 742,
Thiono esters 743, 744
in radical reactions, 961, 980 Triisopropylsilyl
reductive deoxygenation of, 433–435 as hydroxyl protective group, 264–266
Thionyl chloride Trimethylsilyl
reaction with alcohols, 217–218, 223 as hydroxyl protective group, 264
Tiffeneau-Demjanov reaction, 891 Trimethylsilyl iodide (TMSI)
Tin cleavage of ethers by, 240–241
enolates in aldol reactions, 76–78, 128–132 dealkylation of estes, 240
Tin, organo- compounds 2-(trimethylsilyl) ethoxymethyl (SEM)
allenyl Hydroxy protective group, 260, 262, 264
reactions with aldehydes, 850–852 Troc, see trichloroethoxycarbonyl
in synthesis of discodermolide, 1233 Triphenylphosphine