Tom Rovis holds the John K. Stille chair in Chemistry at the Colorado State University, Fort Collins (USA). He graduated from the University of Toronto (Canada) in 1998 and studied with David Evans at Harvard University, before joining the faculty of Colorado State. Among other scientific awards, he received the Roche Excellence in Chemistry Award in 2010. He is a Fellow of the AAAS, Excecutive Editor for the Encyclopedia of Reagents for Organic Synthesis, and Associate Editor for the journal Synlett.
Spurred by the desire to make chemistry a sustainable and "e;greener"e; technology, the field of organocatalysis has grown to become one of the most important areas in synthetic organic chemistry. Organic catalysts can often replace potentially toxic metal catalysts and allow reactions to proceed under mild reaction conditions, thereby saving energy costs and rendering chemical processes inherently safer. More importantly perhaps, organocatalysis offers a complementary reactivity in many instances leading to increased versatility. This Handbook describes 126 key reagents for organocatalytic reactions and will be especially useful for professionals in the area of sustainable chemistry, medicinal research, as well as synthetic organic chemists working in academia and the pharmaceutical industry. All the information compiled in this volume is also available in electronic format on Wiley Online Library. The 126 reagents represented here are but a small fraction of the ca. 5,000 reagents available in the electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS). e-EROS offers various search interfaces to locate reagents of interest, including chemical structure, substructure and reactions search modes. e-EROS is updated regularly with new and updated entries.
Tom Rovis holds the John K. Stille chair in Chemistry at the Colorado State University, Fort Collins (USA). He graduated from the University of Toronto (Canada) in 1998 and studied with David Evans at Harvard University, before joining the faculty of Colorado State. Among other scientific awards, he received the Roche Excellence in Chemistry Award in 2010. He is a Fellow of the AAAS, Excecutive Editor for the Encyclopedia of Reagents for Organic Synthesis, and Associate Editor for the journal Synlett.
Handbook of Reagents for Organic Synthesis: Reagents for Organocatalysis 1
Contents 9
Preface 13
Introduction 15
Catalyst Finder 17
Recent Review Articles and Monographs 21
Short Note on InChIs and InChIKeys 23
A 25
4-Acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl 25
4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate 26
Original Commentary 28
First Update 29
Second Update 31
2'-Amino-[1,1'-binaphthalen]-2-ol 37
(9R)-9-Amino-9-deoxyquinidine 40
Original Commentary 40
First Update 41
(9S)-Amino-9-deoxyquinine 48
Original Commentary 48
First Update 51
(1R,2S)-1-Amino-2,3-dihydro-1H-inden-2-ol 59
Original Commentary 59
First Update 62
(2S,4S)-2-(Anilinomethyl)-1-ethyl-4-hydroxypyrrolidine 74
(S)-2-(Anilinomethyl)pyrrolidine 75
Original Commentary 76
First Update 76
Second Update 80
9-Azabicyclo[3.3.1]nonane-N-oxyl 83
B 85
Benzoyl trimethylsilane 85
Benzyl 1,3-Butadiene-1-carbamate 90
Original Commentary 90
First Update 91
3-Benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium Chloride 93
Original Commentary 93
First Update 94
(S)-5-Benzyl-2-mesityl-6,6-dimethyl-6,8-dihydro-5H-[1,2,4]triazolo[3,4-C][1,4]-oxazin-2-ium Tetrafluoroborate 96
3-Benzyl-4-methyl-1,3-thiazolium Chloride 99
cis-4-Benzyloxy-?,?-bis-(3,5-dimethylphenyl)-L-prolinol (2S,4R)- 100
N-Benzylquininium Chloride 102
Original Commentary 102
First Update 103
Second Update 104
3-Benzylthiazolium Bromide 109
Benzyltriethylammonium Chloride 110
Bicyclo[2.2.1]heptan-2-one, 7,7-Dimethyl-1-(1S,3S,4R)-2-thiabicyclo-[2.2.1]hept-3-yl-, (1S,4R) 112
[1,1'-Binaphthalene]-2,2'-diol, 3,3'-Bis [3,5-bis(trifluoromethyl)phenyl]-, (1R)- 119
N,N'-(1S)-[1,1'-Binaphthalene]-2,2'-diy lbis-(2S,2'S)-pyrrolidine-2-carboxamide 122
(R)-1,1'-Bi-2,2'-naphthol 125
Original Commentary 125
First Update 129
Second Update 134
Third Update 140
1,1'-Binaphthyl-2,2'-disulfonic Acid 148
1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate 153
Original Commentary 154
First Update 154
N,N'-Bis[3,5-bis(trifluoromethyl)-phenyl]thiourea 157
1-[3,5-Bis(tert-butyl)phenyl]octahydro-3,6,6-trimethylcyclopenta[b]phosphole 161
1,3-bis(2,6-diisopropylphenyl)-4,5 dihydroimidazol-2-ylidene 163
Original Commentary 164
First Update 165
1,3-Bis(2,6-diisopropylphenyl)imidazolidinium Chloride 170
1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene 173
Original Commentary 174
First Update 174
(?)-(4R,5R)-4,5-Bis[hydroxy(diphenyl)-methyl]-2,2-dimethyl-1,3-dioxolane (TADDOL) 176
Original Commentary 177
First Update 182
(2S,5S)-2-(Bis(4-methoxyphenyl)((trimethylsilyl)oxy)methyl)-5-(4-methoxy-3,5-dimethylphenyl)pyrrolidine 185
(3R,5R,8R)- 3,8-Bis(1-methylethyl)-2,2,7,7-tetrakis(4-methylphenyl)-1,4,6,9-tetraaza-5?5-phosphaspiro[4,4]non-5-ene, Hydrochloride salt (1:1) 186
1,2-Bis(phenylsulfonyl)ethylene 187
Original Commentary 187
First Update 188
Second Update 190
3,3'-Bis(trifluoromethanesulfonyl)-2,2'-dihydroxy-1,1'-binaphthalene 196
1-[Bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene 198
Original Commentary 199
First Update 202
3-[[3,5-Bis(trifluoromethyl)phenyl]-amino]-4-[[(1R,2R)-2-(dimethylamino)-cyclohexyl]amino]-3-cyclobutene-1,2-dione 204
N-[3,5-Bis(trifluoromethyl)phenyl]-N'-(9R)-cinchonan-9-yl-thiourea 207
N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(1R,2R)-2-(dimethylamino)cyclohexyl]-thiourea 210
1-[3,5-Bis(trifluoromethyl)phenyl]-3-{(2S)-3,3-dimethyl-1-[(triphenylphosphoranylidene)amino]butan-2-yl}thiourea 213
2-[Bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl]pyrrolidine 216
Original Commentary 217
First Update 218
(1R)-3,3'-Bis(2,4,6-trimethylphenyl)-[1,1'-binaphthalene]-2,2'-dicarboxylic acid 223
Bromamine-T 226
Bromonitromethane 229
Original Commentary 229
First Update 231
tert-Butyl 2-(tert-butyldimethylsilyl)-2-oxoacetate 234
(S)-5-((tert-Butyldimethylsilyloxy)-diphenylmethyl)-2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium Tetrafluoroborate 1a (and Related Reagents) 238
C 243
Chloramine-T 243
Original Commentary 243
First Update 244
Second Update 247
Cinchonanium, 1-(9-Anthracenylmethyl)-9-(propen-1-yloxy)-, Bromide (1:1), (8?,9R) 251
Original Commentary 251
First Update 255
1,2-Cyclohexanediamine, N1,N2-Bis[4-(1-pyrrolidinyl)-2-quinolinyl]-, (1R,2R)- 259
D 265
1,4-Diazabicyclo[2.2.2]octane 265
Original Commentary 265
First Update 267
1,3-Di-tert-butylimidazol-2-ylidene 271
Diethyl 1,4-Dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate 278
Diethyl Oxomalonate 285
Original Commentary 285
First Update 287
1,3-Dihydro-1,3-bis(tricyclo[3.3.1.13,7] dec-1-yl)-2H-imidazol-2-ylidene 294
1,3-Dihydro-4,5-dimethyl-1,3-bis(1-methylethyl)-2H-imidazol-2-ylidene 297
4,5-Dihydro-4-phenyl-3H-dinaphtho[2,1-c:1',2'-e]phosphepin 301
2,3-Dihydro-2-phenylimidazo[2,1-b]benzothiazole 304
Original Commentary 305
First Update 306
6,7-Dihydro-2-phenyl-5-(phenylmethyl)-5H-pyrrolo[2,1-c]-1,2,4-triazolium Chloride 310
Original Commentary 310
First Update 314
(R)-2,2'-Dihydroxy-3,3'diphenyl-1,1'-binaphthyl 325
1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene 328
1,3-Dimesityl-1H-imidazolium Salts and 1,3-Dimesityl-imidazolylidene 330
4-Dimethylaminopyridine 333
Original Commentary 333
First Update 335
2,2-Dimethyl-1,3-dioxan-5-one 339
Dimethyldioxirane 344
Original Commentary 345
First Update 348
(11bR)-4-(1,1-Dimethylethyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepin 351
[4S-(4?,5?)]-1-(1,3-Dimethyl-2-oxido-4,5-diphenyl-1,3,2-diazaphospholidine-2-yl)piperidine 354
(1R,2S,4R,5S)-2,5-Dimethyl-7-phenyl-7-phosphabicyclo[2.2.1]heptane 358
1,4-Dimethyl-1H-1,2,4-triazol-4-ium Iodide 359
(11bR)-Dinaphtho[2,1-d:1',2'-f][1,3,2] dioxaphosphepin, 2,6-Bis[3,5-bis (trifluor omethyl)phenyl]-4-hydroxy-, 4-Oxide 363
(11bR)-Dinaphtho[2,1-d:1',2'-f][1,3,2] dioxaphosphepin, 4-Hydroxy-2,6-di-2-naphthalenyl-, 4-Oxide 367
Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 4-Hydroxy-2,6-diphenyl-, 4-Oxide, (11bR)- (Family of Reagents) 369
Original Commentary 371
First Update 372
5,6-Dioxaspiro[2.4]heptane-4,7-dione 375
2,2'-Diphenyl-[3,3'-biphenanthrene]-4,4'-diol (VAPOL) and 3,3'-Diphenyl-[2,2'-binaphthrene]-1,1'-diol (VANOL) 377
Original Commentary 377
First Update 381
?,?-Diphenyl-2-pyrrolidinemethanol 389
Original Commentary 389
First Update 391
Dispiro[2H-pyran-2,4'-[4H-5,6,8b]-triazaacenaphthylene-7'(5'H),2''-[2H]-pyran], 1',2',2'a,3,3',3'',4,4'',5,5'',6,6'',8',8'a-tetradecahydro-1',2'-dimethoxy-6,6''-dimethyl-, monohydrochloride, (1'S,2R,2'S,2''R,2'aS,6S,6''S,8'aS)- 396
N-[(4-Dodecylphenyl)sulfonyl]-2-pyrrolidinecarboxamide (Hua Cat) 397
Dodecyl 4-[[[(2S)-2-pyrrolidinylcarbonyl]- amino]sulfonyl]benzoate (Hua Cat II) 400
H 403
(11bR)-4-Hydroxy-2,6-bis[2,4,6-tris-(1-methylethyl)phenyl]-dinaphtho[2,1-d: 1',2'-F][1,3,2]dioxaphosphepin-4-oxide, [(R)-TRIP] & (11bS)-4-Hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-dinaphtho[2,1-d: 1',2'-f][1,3,2]dioxaphosphepin-4-oxide, [(S)-TRIP]
N-[(1S)-1-(Hydroxydiphenylmethyl)-3-methylbutyl]-2-pyrrolidinecarboxamide 417
trans-4-Hydroxy-L-proline 419
(4aR,9aS)-4-Hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one 423
1H-Imidazolium, 1,3-Bis[2,6-bis-(1-methylethyl)phenyl], tetrafluoroborate(1-) 424
I 427
Iron(2+), tris(2,2'-bipyridine-N,N')-, Dibromide, (OC-6-11) 427
?-Isocupreidine (?-ICD) 430
M 435
1-Mesityl-3,4-dimethyl-4H-1,2,4-triazol-1-ium Tetrafluoroborate 435
9-Mesityl-10-methylacridinium Perchlorate 437
Original Commentary 437
First Update 439
6'-Methoxy-(8S,9R)-cinchonan-9-yl-N-tert-butoxycarbonyl-2-pyrrolidinecarboxylate 441
1-Methyl-2-azaadamantane N-Oxyl 444
(S)-1-Methyl-2-[(dihydroisoindol-2-yl)methyl]pyrrolidine 445
2-Methyltetrahydrofuran 446
Methyl(trifluoromethyl)dioxirane 452
Original Commentary 452
First Update 454
Second Update 457
Methyl Vinyl Ketone 462
Original Commentary 462
First Update 468
N 473
D-2-Naphthylalanine, N,N'-[[(2S, 5S)-1-(4-pyridinyl)-2,5-pyrrolidinediyl]dicarbonyl]bis-, 3,3'-Dioctyl Ester and L-2-Naphthylalanine, N,N'-[[(2S,5S)-1-(4-pyridinyl)-2,5-pyrrolidinediyl]dicarbonyl]bis-, 3,3'-Dioctyl Ester 473
Nitroethane 475
Original Commentary 475
First Update 479
4-Nitropyridine N-oxide 484
P 489
(2S)-N-(2,3,4,5,6-Pentafluorophenyl)-2-pyrrolidinecarboxamide 489
1,5-Pentanediamine, N,N'-Bis[(11bR)-3,5-dihydro-3,5-dimethyl-4-oxido-4H-dinaphtho[2,1-d:1',2'-f]-[1,3,2]diazaphosphepin-4-yl]-N,N'-dimethyl 490
2-Phenyl-6,10b-dihydro-4H,5aH-5-oxa-3,10c-diaza-2-azonia-cyclopenta[c]fluorene tetrafluoroborate 2-Pentafluorophenyl-6,10b-dihydro-4H,5aH-5-oxa-3,10c-diaza-2-azoniacyclopenta[c]fluorene tetrafluoroborate
Original Commentary 499
First Update 505
(8?,9R)-(8''?,9''R)-1,1''-[1,3-Phenylenebis(methylene)]bis[9-hydroxycinchonanium] Dibromide and (9S)-(9''S)-1,1''-[1,3-Phenylenebis(methylene)]bis[9-hydroxycinchonanium] Dibromide 510
2-(Phenylmethoxy)acetaldehyde 513
(S)-Proline 518
Original Commentary 518
First Update 521
Second Update 528
(2S)-2-Pyrrolidinemethanol-?,?-bis(3,5-dimethylphenyl) and (2R)-2-Pyrrolidinemethanol-?, ?-bis(3,5-dimethylphenyl) 541
1-(2-Pyrrolidinylmethyl)pyrrolidine 544
4-(1-Pyrrolidinyl)pyridine 549
5H-Pyrrolo[2,1-c]-1,2,4-triazolium, 7-Fluoro-6,7-dihydro-5-(1-methylethyl)-2-(2,3,4,5,6-pentafluorophenyl)-, (5R,7R)-, Tetrafluoroborate(1-) 552
Q 555
Quinine 555
Original Commentary 555
First Update 557
3-Quinuclidino 571
Original Commentary 571
First Update 572
R 575
Ruthenium (II), Tris(2,2'-bipyrazine-?N1,?N1'), (OC-6-11) 575
Ruthenium(II), Tris(2,2'-bipyridine-?N1,?N1')-, (OC-6-11) 578
Ruthenium(II), Tris(1,10-phenanthroline-?N1,?N10)-, (OC-6-11)- 583
S 585
4,4'-Spirobi[4H-dinaphth[2,1-c:1',2'-e]-azepinium],3,3',5,5'-tetrahydro- 2,6-bis(3,4,5-trifluorophenyl), bromide 585
Spiro[6H-1,3-dioxolo[4,5-c]pyran-6,5'-oxazolidine]-3'-carboxylic acid, tetrahydro-2,2-dimethyl-2',7-dioxo-, 2-methyl-2-propyl ester, (3aR, 5'S, 7aR)- 591
Squaramide 595
T 599
Tetrachlorosilane 599
Original Commentary 599
First Update 600
Second Update 602
2,3,5,6-Tetrahydro-2,6-bis(phenylmethyl)-1H-imidazo[1,2-a]imidazole 606
2,2,6,6-Tetramethylpiperidin-1-oxyl 607
Original Commentary 607
First Update 608
Second Update 611
Third Update 613
(S)-2-(5-1H-Tetrazolyl)pyrrolidine and (R)-2-(5-1H-Tetrazolyl)pyrrolidine 619
Original Commentary 619
First Update 620
Second Update 625
1,2,4-Triazolo[4,3-?]pyridinium,5,6,7,8-tetrahydro-2-(2,3,4,5,6-pentafluorophenyl)-, Tetrafluoroborate 627
Triflimide 628
Original Commentary 629
First Update 631
N-[4-(Trifluoromethyl)benzyl]-cinchoninium Bromide 636
3-(2,4,6-Trimethylphenyl)-1-methyl-1Hbenzo[d]imidazol-3-ium Iodide 638
(5S)-2,2,3-Trimethyl-5-(phenylmethyl)-4-imidazolidinone 640
Original Commentary 641
First Update 642
1,5,7-Trimethyl-7-(5,6,7,8-tetrahydronaphth[2,3-d]oxazol-2-yl)-3-azabicyclo-[3.3.1]nonan-2-one 645
2-Triphenylmethylpyrrolidine 648
Tris[(trifluoromethyl)sulfonyl]methane and Related Salts 649
L-Tryptophan, N,N'-[[(2S,5S)-1-(4-pyridinyl)-2,5-pyrrolidinediyl]-dicarbonyl]bis-, 3,3'-dioctyl Ester 652
Original Commentary 652
First Update 655
U 657
Urea,N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(8a,9S)-6'-methoxycinchonan-9-yl]- Urea,N-[3,5-Bis(trifluoromethyl)phenyl]-N'-(9R)-cinchonan-9-yl-
List of Contributors 663
Reagent Formula Index 679
Subject Index 683
General Abbreviations 725
End User License Agreement 727
| Erscheint lt. Verlag | 20.10.2016 |
|---|---|
| Sprache | englisch |
| Themenwelt | Naturwissenschaften ► Chemie ► Organische Chemie |
| Naturwissenschaften ► Chemie ► Physikalische Chemie | |
| Technik | |
| Schlagworte | Amino • anilinomethyl • azabicyclo • binaphthalen • catalyst • Chemie • Chemistry • deoxyquinidine • deoxyquinine • dihydro • ethyl hydroxypyrrolidine • Finder • inchis • Introduction • Methods - Synthesis & Techniques • Nachhaltige u. Grüne Chemie • Nachhaltige u. Grüne Chemie • Note • OL • Organische Chemie / Methoden, Synthesen, Verfahren • Organische Synthese • Organokatalyse • oxoammonium tetrafluoroborate • Reagenz • Review • Short • Sustainable Chemistry & Green Chemistry • trimethylsilane |
| ISBN-13 | 9781119061014 / 9781119061014 |
| Informationen gemäß Produktsicherheitsverordnung (GPSR) | |
| Haben Sie eine Frage zum Produkt? |
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