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Solid-phase organik syntheses - Burdges K.

Burdges K. Solid-phase organik syntheses - John Wiley & Sons, 2000. - 283 p.
ISBN 0-471-22824-9
Download (direct link): phaseorganicsynthesis2000.pdf
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of chloromethyl polystyrene, 254 of hydroxethylamines, 161 supported reagents for, 167 Swern, 167, 253 TPAP, 239 Oximino esters, 164 Oxindoles, 33 Oxiranes, 168 Oxone, 170
PAL linker, 204 Palladium catalysis, 25, 124 removal of, 27 Palladium catalysis, 168, 177, 253 procedure for Sonogashira couplings, 142 Parallel syntheses, 195 Pauson-Khand cyclization, 42 Penicillamine, 89, 92 Pentafluorophenol, 35 Peptide syntheses, 18 Perbromide-functionalized resin, 182 Permanganate, polymer supported, 168 Perruthenate, 239 Phase transfer agents, 27, 29
alkylations, 89 Phenols, 106, 153
3-fluoro-4-nitro, 105 Phenylacetylene oligomers, 119, 128 Phenylalkylamines, 84 Phenylisothiocyanate, 8 Phosphines “tagged,” 161 carboxy-tagged, 180 chiral peptidic, 206 supported on polyethylene glycol,
166
tri-2-furfuryl, 45 triphenyl, 45, 124 Phosphonium salts, supported, 253 Photoacoustic spectroscopy, 223 Photolabile linkers, 47 Phthalamide, deprotection on resins by hydrazine, 210 Phthalazinones, 165 Phthalic anhydride as a linking agent, 181
Pictet-Spengler cyclizations, 261 Pins, 9, 195, 224 methacrylic acid/dimethyl-acrylamide-based, 199 Piperazine, 45 Piperidines hydroxy, 185 Platinum catalysis, 52, 54 Polarized optical microscopy, 135 Polyethylene glycol, 15, 26, 45 as a support for reagents, 166 decomposition of, in resins, 64 graft copolymer palladium complex, 169 graft resin, 58, 232 polymer grafts, 221 Polymeric bases, 165 Polymerization, 122 Polymers as reagents in library synthesis, 149
INDEX 275
for quenching/work-up, 173 hyperbranched, 133 polydispersion of, 122, 135 radiation grafted, 197 supported, 38 Polymer-supported reactivity seques-trants, 152 Polysaccharide syntheses, 206 Polystyrene, 232 Polystyrene resins aminomethyl, 18, 152, 165 bead diameter, 220 bromomethyl, 60 chloromethyl, 39 crosslinking of, 220, 221 shrinking of in aqueous solvents, 59 Primary libraries, 82 Privileged templates, 108 Proline
4-oxo, 199 Prostaglandins, 61 Prostoglandins PGE and PGF analogs, 251 PGE2 and PGF2oc, 248 Protease inhibitors, 210 Protodesilylation, 38 Pseudoalkaloids, 263 Pseudodilution, 42 Purines, 200 PyBOP, 163 Pyrazoles, 154, 165 Pyridines, 2-amino, 181 Pyridinium, 11 Pyrimidines, 181 Pyrimidinones, 183 Pyrroles, 86
Pyrrolidinemethanol-based catalysts for organozinc addition reactions, 172
Pyrrolidines, 170
Quatemization, 57
Quinolinones, 4-hydroxy, 185, 186 Quinoxalinones, 84, 93, 99, 102
Radiation grafting, 197 Radical copolymerization, 173 Radical initiators, 255 Raman spectroscopy FT, 222
single bead, FT, 221 Reaction kinetics of solid phase reactions, 224 Reagents, polymer-supported, 162 Receptors tweezer, 18 Reductions of amides by borane, 16 of nitro groups, 10, 84, 93, 96, 99, 101, 106 L-selectride, 251 Reductive alkylations, 34, 84, 88, 89, 91, 199, 258 Reductive aminations. See Reductive alkylations Reissert, 62
Resin capture, 10, 52, 175, 178, 180 Resin cleavage, 18 HF, 251
metathesis, 253
of oligomers from triazene linkers using methyl iodide, 141 of Rink linker, 206 photochemical, 263 TFA, 45, 210 using DIBAL, 68 via Stille coupling, 254 via transesterification, 49, 70 Resins 2-chlorotrityl, 257 bromoketone functionalized, 154 carboxyl-functionalized, 173 guanidine-functionalized, 153 isocyanate-functionalized, 154
276 INDEX
Resins (cont’d) polyamine-functionalized, 152, 155 propylaminomethyl, 127, 128, 138, 140
propylaminomethyl, preparation of, 143
solution-like properties, 232 swelling of, 233 Rhodium catalysis, 206 Rink linker, 36 Rink resin, 9, 35, 41, 45 Rink’s amide, 10, 202
Safety catch linkers, 66 Sarcodictin, 258 Sarcosine, 157 Sasrin linker, 209 Scaffolds, 82, 108 Scandium catalysis, 172 Scandium chloride, 172 Scavengers, 18 dimethyl sulfide as, 202 solid phase reagents as, 152 Schultz, 200, 204 L-Selectride, 251 Sequence doubling strategy, 130 Sequestration enabling reagents, 157 of byproducts, 156 of reactants, 152 polymer-assisted, 157 Sharpless’ epoxidation polymer-supported catalyst for, 170 Shikimic acid, 263
Silver dichromate, polymer supported,
167
Single bead analyses, 221 Size exclusion chromatography, 135 S^Ar, 5, 81, 82, 84, 92, ŌĒ, 96, 104, 108, 175, 202, 204 Sonogashira couplings, 263 Sonogashira reactions, 30,40, 122, 169
Spacers, 9
Spectrophotometric methods to monitor solid phase reactions, 224 Spin echo magic angle spinning, 138 Split-and-mix, 55, 150, 220, 263 Stannanes vinyl, 248
vinyl, supported, 253 Stannous chloride, 10 Staudinger reactions, 166, 206 Stille couplings, 41, 45, 251, 253 ligandless, 47 Strecker reactions, 16 Substitution, nucleophilic aromatic,
81. See SyyAr Sugars, 48
Sulfonamides, 18, 41, 88, 153, 160 acyl, as safety catch linker, 66 Sulfonyl chlorides, 88 Sulfur, abstraction of, 4 Superbases, 165 Supramolecular complexes, 1 Suzuki couplings, 41, 48, 169, 176, 177,200, 251 Sweeteners, 1 Swelling, 46
Swern oxidations, 167, 253
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