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Organic Synthesis workbook li - Bittner C.

Bittner C. Organic Synthesis workbook li - John Wiley & Sons, 2001. - 292 p.
ISBN: 3-527-30415-0
Download (direct link): bittnerorganicsynthesisworkbook2001.pdf
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cyclizations DMPM 26
-5-exo-dig 134, 182 DMSO 47, 196
-5-exo-trig 182 DMS0/C02C12 see Swern
cycloadditions domino radical cyclization 182
-1,2 69 domino reaction 5, 110, 116, 134, 220
Index
287
domino-Heck reaction 220 -as glycosyl acceptor 268
dommo-Knoevenagel-betem- -as glycosyl donor 268
Diels-Alder reaction 110, 116 1,2-glycols 24
DOWEX 50W 199 glycols cleavage 62, 199, 204
dye-sensitizer 68 1 ^-fraws-glycoside 250
ECDI (see WSC) 263 glycosyl acceptor 248
EDAC (see WSC) 263 glycosyl donor
EDC 47, 263 -donor phosphite 252
?-enolate 164,214 -semi-acetal 248
efavirenz 71 -imidate 260
electrophilic aromatic substitution 236, 238 glycosylation
endocyclic double bond 66 -boron trifluoride 261
endoperoxide 69 -stannous triflate 257
ene reaction 11 -TMSOTf 259
enol triflate 6 GM2 245
./3- 60 Grigg s condition 128
a- poxide 270 Grignard reagent 9, 77, 148, 180
epoxide opening 198 Grubbs catalyst 10, 145
epoxidation 197, 223, 202 /2-H-elimination 41, 220
?-silyI ketene acetal 163 H2 63,93,113,132,237
ester 165, 172 H2, Pd/C 113, 132
-ix/j-unsaturated 160 halogen-metal exchange 4, 124
-formation 94 Heck reaction 128
-hydrolysis 205 HF-acetonitrile 154
-methyl 252 HF-pyridine 49, 150
ethyl-CDI see WSC 263 Hg(OAc)2 152
ethyleneammonium diacetate 111 high pressure 64
(S)-2-ethylpiperidine 88 himbacine 85
Et3SiH 126 himbeline 85
Evans aldol addition 142, 161 hirsutine 101
Evans auxiliary 141, 162 histidine 241
Evans-Mislow rearrangement 166 HOBT 47
facial selectivity 116, 227 homoallylic alcohol 42
Felkin selectivity 18 Horner- Wadsworth-Emmons 23, 25, 196
Felkin-Anh model 31, 149 Httnig s base 69, 142, 225, 252
Finkelstein reaction 45 hydrazine 234
Fischer-Helferich activation 273 hydrazine acetate 250
fluoride donor 274 hydrazone 234
free electrons 58 1,2-hydride migration 169
Friedel-Crafts catalysts 200 hydroboration 65, 213
j<?-unsaturated aldehyde 164 -(S)-Alpine Borane 212
ganglioside 245 -rhodium(I) complexes 19
gauche effect 147 hydrogen sulfide 262
geminal vinyl dibromide 170 hydrogenation 64, 93, 113, 132, 191, 200
y-hydroxybutenolide 69 -asymmetric 107
Gilbert-Seyferth phosphonate 25, 169 hydrogenolysis 191,254
Gi'/man-cuprate 61, 181 hydrometalation 38
glycal assembly strategy 265, 268 hydrozirconation 38
glycal epoxide method 265 hyperconjugation 131
glycals yS-hyperconj ugation 66
288
Index
I(coll)2 276 Markovnikovs rule 152
IBX 160 MCPBA 60, 166, 181, 197, 223
IC1 126 Meerweins reagent 235
ICN 126 Meldrum s acid 110
imide 190 mesylate 9
iminium ion 105, 190 meta sense 97
indole 108 metathesis reaction 145
indole alkaloid 101 methoxymethylenation 151
insecticidal activity 138 methylamine 190
insertion 41, 220 methyl tert-butyl ether (MTBE) 74
intersystem crossing 68 Michael reaction 5, 160, 180, 222
iodination 67 Michael system 5, 38
iodine glycosylation 276 mismatched reaction 18
[ ()IPC ] 2B - al ly 1 42 Mitsunobu reaction 49
ipso substitution 130 Mn02 23, 38, 106, 160, 171
irinotecan 121 Mukaiyama reaction 30
isomerization 216 multicomponent reaction 110
isopinocampheyl-borane 43 myxalamide A 157
isopropylidene ketal 253 N, /V - arbo n 1 d i i m i da/x) 1 e 240, 270
Jones reagent 46, 189 7V,0-acetal 126
/?-keto carboxylic acid 104 NaBH4 46, 62, 160
ketone /V-acetyl-D-(+)-galactosamine 245
-a,/?-unsaturated 58 7V-acetyl-galactosamine 265
-prochiral 81 /V- ac e t 1 - g lu os a m i n e 265
KHMDS 6,40 N- acetyl- neuraminic- acid 245
kinetic control 40 Nal04 45,62
KMn04 106 neighboring group effect 202, 249, 261
Knochel cuprate 181 /V-iodiosuccinimide (N1S) 126,219, 276
Knoevenagel condensation 110 nitration 236
Koenigs-Knorr reaction 257 nitrile effect 258
KOfBu 242 nitronium ions 236
LACDAC reaction 268 jV-methylation 99
laurallene 137 /V- m e t h 1 m rph 1 i n e - /V- oxide 24, 129, 168,
Lewis acids 222
-BF3OEt2 30 /V-methylpipera/ine 239
-SnCl2 30 norephedrine 78
-TiCl4 30, 142 Normant-caprate 61, 180
-TMSI 130 /V-pyrrodinyl norephedrine 78
L-fucal 268 nucleophilic addition 65,74, 77
LiAlH4 9, 40, 144, 190 nucleophilic substitution 67, 78, 124, 237,
LiBH4 144, 161 239
LiCl 7,47 /2-nucleosides 200
LiC104 188 olefin metathesis 10,145
Lindlar catalyst 93 -mechanism 146
lithium diisopropylamide 61 organocopper reagents 61
Luche reduction 160 organometallic compound 124
2,6-lutidine 144 organozirconium 38
Lycopodium alkaloids 177 ortho-lithiation 75, 89, 125
macrocyclization 28 0s04 24, 128
manganese dioxide 23, 38, 106, 160, 171 oxalyl chloride see Swern
Index
289
oxaphosphetane 218 /7-nitrophenyl chloroformate 205
oxazaborolidine 68,213 polymer supported reagents 200
oxazolidinones 140, 161 polyoxin J 193
oxazolidine-2-thione 140 porphyrin 68
oxazoline 49 potassium permanganate 106
oxidation PPTS 66
-allylic alcohols 23, 187 prochiral ketone 81
-Dess-Martin 12, 29, 67, 160 propargylic alcohol 219
-IBX 160 protodesilylation 186
-Jones 46, 189 pseudoequatorial position 162
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