Page 1337 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1314 Magnesium, organo- compounds (Cont.) Michaelis-Arbuzov reaction, 233
pyridine-2-thiol esters, 638 Mitsunobu reaction
Index sulfonates, 636–637 conversion of alcohols to iodides, 220–221
triethyl orthoformate, 638 glycosylation by, 231
structure and composition, 623–624 inversion of alcohol configuration by, 228
synthesis using, 619–620, 634–644 phosphite esters, synthesis by, 228
examples, 638–640 sulfonamide, synthesis by, 230
, -unsaturated, rearrangement of, 644 sulfonate esters, synthesis by, 228
Malonate esters MOM, see methoxymethyl
allylation, Pd-catalyzed, 712–714 MOP, see 2-methoxypropyl
alkylation of, 22–24 MTM, see methylthiomethyl
magnesium enolates of Mukaiyama aldol reaction, 82–88
acylation, 152, 154 chelation effects in, 100–101
Malonic acids examples, 87–88
amine-catalyzed condensation reactions or, stereoselectivity, of, 96–101
147–148 Mukaiyama-Michael reaction, 190–193
decarboxylation of, 23–24 in Baccatin III synthesis, 1218
Mandelate esters as chiral auxiliaries for in juvabione synthesis, 1181
Diels-Alder reaction, 501 Multistep synthesis
Manganese dioxide, as oxidant, 1068 Baccatin III, 1210–1220
Mannich reaction, 140–145 control of stereochemistry in, 1171–1173
enantioselective, 143–145 convergent steps in, 1163
examples, 141 epothilone a, 1220–1231
Markovnikov’s rule, 290 juvabione, 1174–1186
Meerwein-Pondorff-Verley reduction, 429 longifolene, 1186–1196
N-methylpyrrolidinone Prelog-Djerassi lactone, 1196–1209
as solvent, 18 protecting groups in, 1163
Mem, see 2-methoxyethylmethyl retrosynthetic analysis in, 1164–1166
Mercuration synthetic equivalents in 1163, 1166–1171
aromatic, 1026
electrophilic, cyclization by, 324–328
initiation of polyenes cyclization by, 865 NB-enantride, see borohydrides, alkyl
Mercury, organo- compounds Nickel, organo- compounds, 754–759
carbenes from, 916, 930 allyl complexes, 754, 768
cyclopropanation by, 930 coupling of allylic halides, 754, 755
preparation coupling of aryl halides, 756
from boranes, 652 cross-coupling of organometallic reagents, 758
by oxymercuration, 294–298 Nitration, aromatic, 1004–1008
radicals from, 959 acetyl nitrate for, 1005
reaction with examples, 1006–1009
acyl chlorides, 663 lanthanide catalysis of, 1005–1006
reduction by NaBH 4 , 295 nitrogen dioxide and ozone for, 1006–1008
reduction by Bu 3 SnH, 319 transfer, 1006–1008
Metallocarbenes, see carbenes, metallo- trifluoroacetyl nitrate for, 1005
Methane Nitrenes, 944–947
polyhalo generation from azides, 944
carbenes from, 914 reactions, 946–947
2-methoxyethoxymethyl singlet, 944
hydroxy protective group, 260 triplet, 944
Methoxymethyl Nitrile oxides
hydroxyl protective group, 260 dipolar cycloaddition, 535–538
Bis-1,2-[(2-methoxyphenyl) in epothiolone a synthesis, 1229–1230
phenylphosphino]ethane Nitriles
ligand in enantioselective hydrogenation, 380 carbanions from, 65
2-methoxypropyl -alkoxy, as nucleophilic acyl
hydroxy protective group, 259–260 equivalents, 1168
Methylthiomethyl alkylation, 34
hydroxy protective group, 260–261 reaction with chromium tricarbonyl
Michael reaction, see conjugate addition complexes, 769–770