List of Abbreviations
acac:
Acetylacetone
AcBr:
Acetyl bromide
AcCl:
Acetyl chloride
AcOEt:
Ethyl acetate
AcONa:
Sodium acetate
AD-mix-β:
Sharpless dihydroxylation reagent
AIBN:
Azobisisobutyronitrile
BAIB:
Bis(acetoxyiodo)benzene
9-BBN:
9-Borabicyclo[3.3.1]nonane
BHT:
2,6-di-
tert
-Butyl-4-methylphenol
BINOL:
1,1’-bis-2-Naphthol
Bmim:
1-Butyl-3-methylimidazolium
Bn:
Benzyl
Bn-Br:
Benzyl bromide
Bn-OH:
Benzyl alcohol
BOP:
Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate
n
-BuOH:
n
-Butanol
t
-BuOH:
tertio
Butanol
Bu
2
SnO:
Dibutyltin oxide
Bz:
Benzoyl
CAN:
Ceric ammonium nitrate
CBS:
Corey–Bakshi–Shibata reagent
CM:
Cross-metathesis
Coll:
Collidine
Comins’ reagent:
2-[
N,N
-Bis(trifluoromethanesulfonyl)amino]-5-chloropyridine
15-Cr-5:
Ether crown with 15 atoms including 5 oxygen
18-Cr-6:
Ether crown with 18 atoms including 8 oxygen
CSA:
Camphorsulfonic acid
DABCO:
Diazabicyclo [3.3.3]octane
DBA:
Dibenzylideneacetone
DBU:
1,8-Diazabicyclo[5.4.0]undec-7-ene
DCC:
Dicyclohexylcarbodiimide
DCE:
1,2-Dichloroethane
DDQ:
2,3-Dichloro-5,6-Dicyanoparaquinone
DEAD:
Diethyl azodicarboxylate
DET:
Diethyl tartrate
DHP:
Dihydropyrane
DHQD:
Dihydroquinidine
DIAD:
Diisopropyl azodicarboxylate
DIBAL:
Diisobutylaluminum hydride
DIC:
Diisopropylcarbodiimide
DIPEA:
Diisopropylethylamine
DIPT:
Diisopropyl tartrate
DMA:
Dimethylacetamide
DMAP:
4-Dimethylaminopyridine
DMDBA:
Bis(3,5-dimethoxybenzylidene)acetone
DME:
Dimethoxyethane, glyme, monoglyme
DMF:
Dimethylformamide
DMIPS:
Dimethylisopropylsilyl
DMP:
Dess–Martin periodinane
DMPU:
Dimethylpropyleneurea
DMSO:
Dimethyl sulfoxide
DOSP:
Dodecylbenzenesulfonyl-
(S)
-prolinate
Equiv.:
Equivalent
Et
2
O:
Diethylether
Et
3
N:
Triethylamine
Fmo:
9-Fluorenylmethyloxy
GB
II
:
Second-generation Grubbs catalyst
HG:
Hoveyda–Grubbs catalyst
HG
II
:
Hoveyda–Grubbs catalyst (second generation)
HMPA:
Hexamethylphosphoramide
HMTA:
Hexamethylenetetramine
Imid.:
Imidazole
Ipc:
Isopinocampheyl
i
-Pr
2
NEt:
Diisopropylethylamine
i
-Pr
2
NH:
Diisopropylamine
KHMDS:
Potassium bis(trimethylsilyl)amide
LDA:
Lithium diisopropylamide
LiHMDS:
Lithium bis(trimethylsilyl)amide
LiTMP:
Lithium tetramethylpiperidide
L-Selectride:
Lithium tri-(2s)-2-butanyl(hydrido)borate
2,6-Lutidine:
2,6-Dimethylpyridine
m
-CPBA:
meta
-Chloroperoxybenzoic acid
MeCN:
Acetonitrile
Me-I:
Methyl iodide
MeOH:
Methanol
MeO-Na:
Sodium methoxide
MIB:
3-
exo
-Morpholinoisoborneol
MOM:
Methoxymethyl
Ms-Cl:
Methanesulfonyl chloride
NaHMDS:
Sodium bis(trimethylsilyl)amide
NBS:
N
-Bromosuccinimide
NIS:
N
-Iodosuccinimide
NMO:
N
-Methylmorpholine N-oxide
Oxone:
Potassium peroxymonosulfate: KHSO
5
PBu
3
:
Tributylphosphine
PDC:
Pyridinium dichromate
Ph-H:
Benzene
Ph-Me:
Toluene
Piv-Cl:
Pivaloyl chloride
PMB:
p
-Methoxybenzyl
PPh
3
:
Triphenylphosphine
PPTS:
Pyridinium
p
-toluenesulfonate
n
-PrOH:
n
-Propanol
RCM:
Ring-closing metathesis
r.t.:
Room temperature
SET:
Single electron transfer
SiMe
3
:
Trimethylsilyl
TBAF:
Tetra-
n
-butylammonium fluoride
TBAI:
Tetrabutylammonium iodide
TBHP:
tert
-Butyl hydroperoxide
TBS or TBDMS:
tert
-Butyldimethylsilyl
TEMPO:
(2,2,6,6-tetramethylpiperidinyl-1-yl)oxy
TES:
Triethylsilyl
TFA:
Trifluoroacetic acid
Tf
2
O:
Triflic anhydride
THF:
Tetrahydrofuran
THP:
Tetrahydropyrannyl
TIPS:
Triisopropylsilyl
TMEDA:
Tetramethylethylenediamine
TMS-Cl:
Trimethylsilyl chloride
TMS-I:
Trimethylsilyl iodide
TMS-OMe:
Methoxytrimethylsilane
TMSOTf:
Trimethylsilyl trifluoromethanesulfonate
TPAP:
Tetrapropylammonium perruthenate (Steve Ley’s reagent)
TPP:
5,10,15,20-Tetraphenyl-[21H,23H]porphine
TPS:
tert
-Butyldiphenylsilyl
Tris-imid:
Trisimidazole
Troc:
2,2,2-Trichloroethoxycarbonyl
TsOH:
p
-Toluenesulfonic acid
Index
A, B, C
acyl selenide, 129, 130, 133
addition, 3–5, 10, 24, 28, 31, 37, 43, 56, 88, 90, 96, 113, 117, 118, 120, 122, 130, 162, 163, 166, 167, 175, 179, 198, 202, 204, 214, 215, 217, 218, 220–223, 236, 237, 243, 244, 254, 282
alkenes, 11, 37, 38, 44, 56, 63, 75, 117, 135, 151–153, 155, 193, 242, 264, 265
enol triflates, 225
Shapiro reaction, 214, 222–225
alkylation, 10, 37, 56, 65, 66, 94, 129, 177, 178, 184, 186, 216, 239, 260
Appel reaction, 105
cycloaddition [2+2] of arynes, 120
diastereoselective alkylation according to Myers, 177
diastereoselective alkylation of oxazolidinones, 68
enantioselective allylation, 193
alkynes
functionalization of true alkynes, 29
Sonogashira reaction, 23, 26, 30, 31, 114, 116, 117
benzocyclobutenols, 124
butyrolactone, 23, 32, 34, 35, 51–53, 55, 60, 94, 213, 219, 273
C-H
activation, 10, 173, 181, 197
carbonylation, 218, 226
Clauson-Kaas reaction, 134, 137
D, E, H
deprotection, 6, 25, 62, 69, 185, 189, 196, 199, 254, 262, 291
Duff reaction, 139
elimination
Grieco elimination, 63, 215, 227
ene reaction between alkynes and alkenes, 85
epoxides, 58, 59, 192
asymmetric epoxidation according to Shi, 151
ester, 24, 27, 34, 36, 60, 83, 87, 104, 129, 130, 146, 149, 160, 163, 166, 173, 185, 193, 197, 202, 249, 262, 274, 277, 278, 283
Mitsunobu reaction in FBS mode, 257
saponification, 216, 258
halogenated, 88, 143
bromoalcohols, 64
bromohydrins, 154
I, K, M
intramolecular [3+2] cycloadditions, 287
iodoetherification, 53, 55, 56
ketalization, 54
Knoevenagel condensation, 283, 288
metathesis, 10, 22, 34, 37–40, 43, 143, 144, 148, 155, 176, 179, 180, 194, 196, 198, 199, 203, 205, 236, 241, 242, 261, 268, 296, 299
domino process, 37
ring-closing metathesis, 34, 160, 173, 176, 179, 194, 197, 199, 204, 234, 241, 250, 258, 259
N, O, P
Negishi coupling, 96, 97, 185
olefination, 251, 253, 254, 259, 264, 265, 267
oxazaborolidine, 71
oxazolidinone, 65, 66, 69, 70
diastereoselective alkylation, 68, 177
oxidation
of aldehydes to carboxylic acids, 57
of primary alcohols to carboxylic acids, 57
Swern oxidation, 74, 163, 164, 195
phosphate, 37, 166, 177, 189, 199
protection, 24, 67, 163, 164, 174, 186, 253, 260
Pyrrole formation, 137
R, S
radical cyclization, 113, 116, 122, 124, 129–133
rearrangement, 24, 27, 28, 42, 59, 149, 172, 177, 180, 183, 184, 187, 190, 191, 198, 201–203, 205, 215, 217, 218, 259, 262, 263, 266
Payne rearrangement, 144, 146, 149, 154
Wolff rearrangement, 60, 62, 63
reduction, 3, 10, 22, 23, 26, 30, 33, 35, 37, 40, 43, 60, 65, 67, 69, 72, 103–106, 114, 116, 117, 125, 128, 129, 131, 134, 139, 143, 144, 148, 160, 163, 168, 169, 173, 178, 186, 196, 199, 200, 216, 234, 237, 242, 243, 251, 252, 260, 262, 264, 265, 267, 277
enantioselective reduction of ketones, 71
reduction of enones according to Luche, 242
rerrangment
sigmatropic rearrangement [3, 3] of propargyl esters, 180
ruthenium, 41, 86, 106, 122, 241
ene reaction catalyzed by ruthenium, 83
Sonogashira reaction, 23, 26, 30, 31, 114, 116, 117
Stille coupling, 83, 85, 88, 101, 102, 104
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