Download 97a Tbl Contents

v
Contents
PREFACE .................................................................................................... xi
LIST OF JOURNALS ABSTRACTED ..................................................... xiv
GLOSSARY OF ABBREVIATIONS ........................................................ xvi
I
CARBON–CARBON BOND FORMING REACTIONS
A Carbon-Carbon Single Bonds (see also: I.E., I.F., I.G., I.H.)… .....1
1 Alkylations of Aldehydes, Ketones, and their Derivatives .......1
2 Alkylations of Nitriles, Acids and Acid Derivatives ................2
3 Alkylations of -Dicarbonyl, -Cyanocarbonyl Systems,
and Other Active Methylene Compounds ................................5
4 Alkylations of N-, P-, S-, Se & Similar Stabilized Carbanions ....7
5 Alkylations of Organometallic and Related Reagents
(see also: I.B.3., I.B.4., I.F., I.G.)..............................................9
6 Other Alkylation Procedures ..................................................12
7 Nucleophilic Addition to Electrophilic Carbon ......................12
a 1,2-Additions ....................................................................12
(1) Aldol-Type 1,2 Additions ..........................................12
(2) Add’n of N, P, S, Se & Similar Stabilized Carbanions ..19
(3) Addition of Organometallic and Related Species ......20
(4) Other 1,2-Additions....................................................31
b Conjugate Additions .........................................................33
(1) Enolate-Type Carbanions ........................................33
(2) Organometallic and Related Reagents .....................35
(3) Other Conjugate Additions ......................................38
8 Other Carbon-Carbon Single Bond Forming Reactions .........40
B Carbon-Carbon Double Bonds (See also: I.E.1) ...........................43
1 Wittig-Type Olefination Reactions.........................................43
2 Eliminations ............................................................................45
a Alcohols and Derivatives..................................................45
b Halides ..............................................................................46
c Other Eliminations............................................................46
3 Olefin Metathesis ....................................................................47
4 Other Carbon-Carbon Double Bond Forming Reactions .......50
5 Vinylations..............................................................................53
6 Allene Forming Reactions ......................................................55
C Carbon-Carbon Triple Bonds .......................................................57
D Cyclopropanations ........................................................................60
1 Carbene or Carbenoid Additions to a Multiple Bond .............60
2 Other Cyclopropanations ........................................................62
E Thermal and Photochemical Reactions ........................................64
1 Cycloadditions ........................................................................64
2 Other Thermal Reactions ........................................................72
vi
II
III
3 Photochemical Reactions ........................................................73
F Aromatic Substitutions Forming a New Carbon-Carbon Bond ....75
1 Friedel-Crafts Type Aromatic Substitution Reactions ...........75
2 Coupling Reactions to Form an Aromatic-Aromatic Bond ....78
3 Other Aromatic Substitutions and Preparations .....................82
G Synthesis via Organometallics ......................................................86
1 Synthesis via Organoboranes ..................................................86
2 Carbonylation Reactions .........................................................88
3 Other Syntheses via Organometallics .....................................91
H Rearrangements ............................................................................95
1 Claisen, Cope and Similar Processes ......................................95
2 Other Rearrangements ............................................................98
OXIDATIONS
A C-O Oxidations ..........................................................................102
1 Alcohol  Ketone, Aldehyde ..............................................102
2 Alcohol, Aldehydes  Acids, Esters ...................................104
B C-H Oxidations ...........................................................................105
1 C-H  C-O ..........................................................................105
2 C-H  C-Hal........................................................................107
C C-N Oxidations ...........................................................................107
D Amine Oxidations .......................................................................108
E Sulfur Oxidations........................................................................109
F Oxidative Additions to C-C Multiple Bonds ..............................110
1 Epoxidations .........................................................................110
2 Hydroxylations .....................................................................113
3 Other Oxidative Additions to C-C Multiple Bonds ..............114
G Phenol-Quinone Oxidation .........................................................115
H Dehydrogenation.........................................................................115
I Other Oxidations ........................................................................116
REDUCTIONS
A C=O Reductions (see also III.F.1) ..............................................118
1 Aldehydes, Ketones  Alcolols...........................................118
2 Acids, Esters, Amides  Aldehydes ....................................120
3 Acids, Ester, Amides  Alcohols ........................................120
B C-N Multiple Bond Reductions ..................................................121
1 Imine Reductions ..................................................................121
2 Reductions of Heterocycles ..................................................123
C Reduction of Sulfur Compounds ................................................123
D N-O Reductions ..........................................................................124
E C-C Multiple Bond Reductions ..................................................125
1 C=C Reductions....................................................................125
2 CC Reductions ....................................................................127
F Hetero Bond Reductions .............................................................128
vii
IV
V
VI
1 C-O  C-H ..........................................................................128
2 C-Hal  C-H........................................................................129
3 C-S  C-H ...........................................................................130
G Reductive Cleavages...................................................................130
1 Oxiranes ................................................................................130
2 N—O Cleavages ...................................................................131
3 Other Reductive Cleavages...................................................132
H Reduction of Azides ...................................................................132
I Other Reductions ........................................................................132
SYNTHESIS OF HETEROCYCLES
A Oxiranes, Aziridines, and Thiiranes ...........................................133
B Oxetanes, Azetidines, and Thietanes ..........................................137
C Lactams .......................................................................................137
D Lactones ......................................................................................146
E Furans and Thiophenes ...............................................................151
F Pyrroles, Indoles, etc ...................................................................159
G Pyridines, Quinolines, etc ...........................................................167
H Pyrans, Pyrones, and Sulfur Analogues ......................................174
I Other Heterocycles with One Heteroatom ..................................179
J Heterocycles with a Bridgehead Heteroatom .............................180
K Heterocycles with Two or More Heteroatoms ............................183
1 Heterocycles with 2 N’s........................................................183
a 5-Membered....................................................................183
b 6-Membered....................................................................188
c 7-Membered....................................................................191
2 Heterocycles with 2 O’s or 2 S’s ..........................................192
3 Heterocycles with 1 N and 1 O .............................................193
4 Heterocycles with 1 N and 1 S .............................................199
5 Heterocycles with 1 O and 1 S .............................................202
6 Heterocycles with 3 or more N’s ..........................................203
7 Heterocycles with 2 N’s and 1 O ..........................................206
8 Heterocycles with 2 N’s and 1 S or 1 Se ..............................206
L Other Heterocyles .......................................................................207
M. Reviews .......................................................................................209
PROTECTING GROUPS ..................................................................
A Aldehyde and Ketone Protecting Groups ...................................215
B Amino Acid Protection ...............................................................217
C Amine Protecting Groups ...........................................................217
D Carboxyl Protecting Groups ......................................................220
E Hydroxyl Protecting Groups .......................................................221
F Other Protecting Groups .............................................................224
USEFUL SYNTHETIC PREPARATIONS
A Functional Group Preparations ...................................................225
1 Acetals and Ketals ...............................................................225
viii
2 Acids and Anhydrides (see also: I.A.2, II.B.1, V.E) ............228
3 Alcohols & Related Species (see also: II.B.1, III.A., V.E., VI.A.11) ... 229
4 Aldehydes and Ketones (see also: I.A.1., I.G.2., II.A.1 .......231
5 Amides and Related Species................................................233
6 Amines ................................................................................237
7 Amino Acid Derivatives ......................................................241
8 Azides ..................................................................................246
9 Carbohydrates ......................................................................246
10 Esters (see also: I.G.2., IV.D., V.D., VI.A.3) ......................248
11 Ethers ...................................................................................250
12 Halides (see also: II.B.2.).....................................................253
13 Nitriles and Imines...............................................................256
14 Other N-Containing Functional Groups ..............................257
B Additions to Alkenes and Alkynes .............................................259
C Boron Compounds ......................................................................260
D Nucleosides, Nucleotides etc ......................................................261
E Phosphorus, Selenium and Tellurium Compounds ....................263
F Silicon Compounds ....................................................................267
G Sulfur Compounds ......................................................................269
H Tin Compounds ..........................................................................272
VII REVIEWS (see also: IV.M, VIII.A.5; VIII.C.7)
A Techniques .................................................................................274
B Asymmetric Synthesis and Molecular Recognition ....................276
C Reactions ....................................................................................281
D Reactive Intermediates................................................................284
E Organometallics and Metalloids .................................................287
F Halogen Compounds and Halogenation (see also: VI.A.10) ......293
G Natural Products .........................................................................294
H Others (see also: IV.M, VIII.A.5, VIII.C.6, VIII.F.7) .................299
VIII SELECTED TOPICAL AREAS
A Fullerene Chemistry....................................................................306
1 Diels-Alder Type Cycloadditions .........................................306
2 Other Cycloadditions ............................................................306
3 Photochemical Reactions ......................................................307
4 Other Fullerene Chemistry ...................................................308
5 Reviews ................................................................................311
B Taxol and Related Taxane Chemistry.........................................312
C Dendrimers, Calixarenes and Other Unnatural Products ............315
1 Dendrimers ...........................................................................315
a Dendrimer Synthesis .......................................................315
b Dendrimer Catalysts .......................................................318
c Hetero-Containing & Miscellaneous Dendrimers ..........318
2 Calixarenes ...........................................................................319
a Calixarene Receptors ......................................................319
ix
b Synthesis of Calixirene ...................................................320
c Synthesis on Calixirenes .................................................322
d Calixirene Isolation, Conformation, etc .........................323
3 Rotaxanes .............................................................................324
4 Supramolecules .....................................................................326
5 Cyclophanes ..........................................................................328
6 Other .....................................................................................328
7 Reviews ................................................................................329
D Total Syn. of Selected Natural Products (see also: VIII.B) ................ 329
E Reactions in Polar Media ............................................................346
1 Reactions in Aqueous Media ................................................346
2 Reactions in Ionic Media ......................................................351
F Combinatorial Chemistry ...........................................................362
1 Supports, Linkers & Protecting Groups................................362
2 Supported Reagents, Catalysts Ligands & Scavengers.........364
3 Solid-Phase Heterocyclic Synthesis......................................368
4 Solid -Supported Organic Reactions ....................................372
5 Targeted Library Synthesis ...................................................375
6 Novel Techniques in Combinatorial Chemistry ...................377
7 Reviews ................................................................................379
AUTHOR INDEX.......................................................................................381