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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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Danishefsky’s diene, 156 DDQ, 181
Debromination, reductive, 37 Deconvolution, 196 Dehydration reactions, 166 Dehydroquinoxalinones, oxidation of, 104
Deletion intermediates, 159 Demethylation, 260 Dendrimers, 133 Desilylation, 39, 153, 253 Dialkylimidodithiocarbonimidate, S,S,3
Diatomacious earth, 174 Diazonium salts, 127 preparation of, 143 DiBAL, as resin cleavage agent, 68 Diboronic acids, 55 DIC,45,88
Dichromate, polymer-supported, 182 Dieckmann cyclizations, 179, 185 Diffuse reflectance infra red Fourier transform spectroscopy, 223 Dihydropyridines, 84 Diketopiperazines, 16, 260, 261 indolyl, 260 Diltiazem, 84
Dinitrofluorobenzene, 2,4-, 6 Dioxiranes methyl(trifluoromethyL), 253 trifluoromethyl, 170 Directed orthometalation, 71
Disuccinimidocarbonate, 106 Divergent-convergent approach to oligomers, 121 Diversity, 35, 109 DNA, 16
EDC, 20
Elemental analysis, 140 Elimination, 55
Ellman, 47, 50, 55, 60, 61, 66, 67,
104, 109, 172, 200, 204, 251 Enamines, 86, 88 Encoding, 89, 150 of pins, 211 radiofrequency, 257 Epothilone A, 251 Epoxides, ring opening, 170
Fischer indole synthesis, 30 Fluorimetric methods to monitor solid phase reactions, 224 Fluorous phase, 26, 175 Fluorous phase chromatograpic support, 175 Focused libraries, 82 Formic acid as a reductant, 56 Fragment condensation, 120, 121 FTIR, 136,219 microspectroscopy, 221 single bead, 224
to monitor solid phase reactions, 220 Fumitremorgins, 260
Genomics, 150 Gilbertson, 206 Glutamic acid, 257 Glycine, 157 allyl, methylester, 41 Grignard reactions, 64, 174
272 INDEX
Grubbs’ catalysts, 253, 255 Guanidines, 1 bicyclic, 16 oligo, 16
PMC-protected, 68 polymer-supported, 166 retrosynthetic analyses, 2 supported, 180 syntheses on pins, 205 Guanidinylating agents pyrazole derivatives, 6, 14, 15 triflylguanidines, 7 Guiles, 50, 52, 57
Hantzsch synthesis, 154 Heck coupling, 169 Heck reactions, 27, 41 intramolecular, 33 Herbicides, 163 Heteroannulation, 32 Heterocycles, benzofused, 81 Heterooligomers, 131 HIV protease, 170 HOBt, 163 Homocysteine, 89, 91 Htinig’s base, 12, 47 Hydride elimination, (3-, 34, 37, 55 Hydroboration, 50, 60 Hydroformylation, 206 Hydrogenations, 255 Lindlar, 248 Hydroxamic acids, 99, 210 Hydroxamic esters, 164 Hydroxybenzotriazole, 163 Hydroxy methyl polystyrene, 258 Hydrozirconations of alkynes, 251 Hyperbranching of polymers, 133
Imidocarbonyl dichlorides, 2, 3 Imines, 86
Immobilized catalysts, 26 Indoles, 35, 37, 165 3-acetic acid, 34 Fischer synthesis, 30 Infrared, 10, 136
Inverse temperature dependence of polymer solubilities, 169 Iodonium salts, 169 Ion exchange resins, 153, 157, 177, 178, 181 Amberlite, 156, 163 Amberlyst, 161 Ipso substitution, 59 with resin cleavage, 60 IR, 10, 136 Isocyanates, 88, 178 benzenesulfonyl, 158, 160 thioazolyl, 160 Isocyanides, 177 Isoquinolines bromo-, 63 isoxazolino, 62 Isoquinolones, 45 Isothiocyanates, 4, 9, 183, 206 acyl, 14 phenyl, 8, 10
trichloroethoxy carbonyl, 16 Iterative reactions, 39
Janda, 248
KBr pellets, 223 Kenner, 66 Ketenes, 58 phenoxy, 57 Ketoesters, (3-, 68 Ketones, p-hydroxy, 61 Knoevenagel condensation, 96 Kurth, 62
INDEX 273
Lactams, 99 Lactams, [3-, 41, 56, 57 Lindlar catalyst, 248 Linkers, 9, 18 carbamate, 41, 66 effects on reaction rates, 236 on crowns, 208 PAL, 204
photolabile, 206, 263 Sasrin, 209 silyl-based, 59, 60 THP, tetrahydropyranyl, 67, 204, 248 tin-based, 254 to generate aldehydes, 209 traceless, 39, 55, 62, 109 traceless, photolabile, 46 traceless, silyl-based, 47 triazenes, 126 trityl, 210, 236 Linking reagents, 157 Liquid crystal, 49 Loading, determination of spectroscopically, 239
Macrocyclization, 42 Magic angle spinning, 42, 64, 101, 138 Mannich reactions, 45 Matrix metalloproteases, 210 Mercaptoacetic acid, 97 Mercuric chloride, 4, 11, 16 Merrifield resin, 12, 18,49, 126, 138, 140
Metathesis, 253 Methanethiol, 5 Methyl iodide, 39 Michael addition, 10 Microcans, 257 Microreactors, 255 Microscopy, 135 Microwave irradiation, 63
Mitsunobu reactions, 8, 10, 12, 30, 161, 166, 185,200, 204, 255 Mixed-resin beds, 174 Mixing effects on reaction rates, 237 Miyaura, 52 Modular chemistry, 61 Moffatt oxidation, 160 Monitoring of polymer syntheses on resins, 136 Mukaiyama’s reagent, 6, 11, 88 Multipin method, 196, 233 Multistep syntheses, 183 Muscone, 255
Nafion, 172 Natural products as scaffolds, 248 solid phase syntheses of, 247 Nicolaou, 253, 255, 258 Nielsen, 261 Nifedipine, 84 NMR COSY, 138 gel phase carbon, 45 gel phase fluorine, 55 magic angle spinning, 42, 64, 101 spin echo magic angle spinning, 138 TOCSY, 42, 138 Noyori, 248
Nucleophilic aromatic substitution,
81. See SNAr Null-to-null IR monitoring, 136
01igo( 1,4-phenyleneethynylene)s. See Phenylacetylene oligomers Oligoguanidine, 16 Oligomers, 119, 128 Oligonucleotides antisense, 16 Optical microscopy, 135
274 INDEX
Organolithium reagents, 173 Organozinc compounds, 70 Orthometalation, directed, 71 Oxalates, 158 Oxazoles, hydro-, 263 Oxazolidinones, 102 Oxazolidones, 93 Oxazoline, 209 Oxidations, 170 Corey-Kim, 255 Dess-Martin, 255, 258 epoxidation and dihydroxylation, 170 Moffatt, 160 NaC102, 258
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