Handbook of Reagents for Organic Synthesis
Reagents for Organocatalysis
Published on 14. October 2016
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Hardback
816 pages
978-1-119-06100-7 (ISBN)
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Description
Spurred by the desire to make chemistry a sustainable and "greener" 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.
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Wiley
€158.99
Available for download
Person
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.
Content
Preface xi
Introduction xiii
Catalyst Finder xv
Recent Review Articles and Monographs xix
Short Note on InChIs and InChIKeys xxi
4-Acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl 1
4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate 2
2[1]-Amino-[1,1[1]-binaphthalen]-2-ol 13
(9R)-9-Amino-9-deoxyquinidine 16
9(S)-Amino-9-deoxyquinine 24
(1R,2S)-1-Amino-2,3-dihydro-1H-inden-2-ol 35
(2S,4S)-2-(Anilinomethyl)-1-ethyl-4-hydroxypyrrolidine 50
(S)-2-(Anilinomethyl)pyrrolidine 51
9-Azabicyclo[3.3.1]nonane-N-oxyl 59
Benzoyl trimethylsilane 61
Benzyl 1,3-Butadiene-1-carbamate 66
3-Benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium Chloride 69
(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 72
3-Benzyl-4-methyl-1,3-thiazolium Chloride 75
cis-4-Benzyloxy-alpha, alpha-bis-(3,5-dimethylphenyl)-L-prolinol (2S,4R)- 76
N-Benzylquininium Chloride 78
3-Benzylthiazolium Bromide 85
Benzyltriethylammonium Chloride 86
Bicyclo[2.2.1]heptan-2-one,7,7- Dimethyl-1-(1S,3S,4R)-2-thiabicyclo-[2.2.1]hept-3-yl-, (1S,4R) 88
[1,1[1]-Binaphthalene]-2,2[1]-diol, 3,3[1]-Bis[3,5-bis(trifluoromethyl)phenyl]-, (1R)- 95
N,N[1]-(1S)-[1,1[1]-Binaphthalene]-2,2[1]-diy lbis-(2S,2[1]S)-pyrrolidine-2-carboxamide 98
(R)-1,1[1]-Bi-2,2[1]-naphthol 101
1,1[1]-Binaphthyl-2,2[1]-disulfonic Acid 124
1,1[1]-Binaphthyl-2,2[1]-diyl Hydrogen Phosphate 129
N,N[1]-Bis[3,5-bis(trifluoromethyl)-phenyl]thiourea 133
1-[3,5-Bis(tert-butyl)phenyl]octahydro-3,6,6-trimethylcyclopenta[b]phosphole 137
1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene 139
1,3-Bis(2,6-diisopropylphenyl)imidazolidinium Chloride 146
1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene 149
(-)-(4R,5R)-4,5-Bis[hydroxy(diphenyl)-methyl]-2, 2-dimethyl-1,3-dioxolane(TADDOL) 152
(2S,5S)-2-(Bis(4-methoxyphenyl)((trimethylsilyl)oxy) methyl)-5-(4-methoxy-3,5-dimethylphenyl)pyrrolidine 161
(3R,5R,8R)- 3,8-Bis(1-methylethyl)-2,2,7,7-tetrakis(4-methylphenyl)-1,4,6,9-tetraaza-5lambda5-phosphaspiro[4,4] non-5-ene, Hydrochloride salt (1:1) 162
1,2-Bis(phenylsulfonyl)ethylene 163
3,3[1]-Bis(trifluoromethanesulfonyl)-2,2[1]-dihydroxy-1,1[1]-binaphthalene 172
1-[Bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene 174
3-[[3,5-Bis(trifluoromethyl)phenyl]-amino]-4-[[(1R,2R)-2-(dimethylamino)-cyclohexyl]amino]-3-cyclobutene-1,2-dione 180
N-[3,5-Bis(trifluoromethyl)phenyl]-N[1]-(9R)-cinchonan-9-yl-thiourea 183
N-[3,5-Bis(trifluoromethyl)phenyl]-N[1]-[(1R,2R)-2-(dimethylamino)cyclohexyl]-thiourea 186
1-[3,5-Bis(trifluoromethyl)phenyl]-3-{(2S)-3,3-dimethyl-1-[(triphenylphosphoranylidene)amino] butan-2-yl}thiourea 189
2-[Bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl) oxy]methyl]pyrrolidine 192
(1R)-3,3[1]-Bis(2,4,6-trimethylphenyl)-[1,1[1]-binaphthalene]-2,2[1]-dicarboxylic acid 199
Bromamine-T 202
Bromonitromethane 205
tert-Butyl 2-(tert-butyldimethylsilyl)-2-oxoacetate 210
(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) 214
Chloramine-T 219
Cinchonanium, 1-(9-Anthracenylmethyl)-9-(propen-1-yloxy)-, Bromide(1:1), (8alpha,9R) 227
1,2-Cyclohexanediamine, N1,N2-Bis[4-(1-pyrrolidinyl)-2-quinolinyl]-, (1R,2R)- 235
1,4-Diazabicyclo[2.2.2]octane 241
1,3-Di-tert-butylimidazol-2-ylidene 247
Diethyl 1,4-Dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate 254
Diethyl Oxomalonate 261
1,3-Dihydro-1,3-bis(tricyclo[3.3.1.13,7]dec-1-yl)-2H-imidazol-2-ylidene 270
1,3-Dihydro-4,5-dimethyl-1,3-bis(1-methylethyl)-2H-imidazol-2-ylidene 273
4,5-Dihydro-4-phenyl-3H-dinaphtho[2,1-c:1[1],2[1]-e]phosphepin 277
2,3-Dihydro-2-phenylimidazo[2,1-b]benzothiazole 280
6,7-Dihydro-2-phenyl-5-(phenylmethyl)-5Hpyrrolo[2,1-c]-1,2,4-triazolium Chloride 286
(R)-2,2[1]-Dihydroxy-3,3[1]diphenyl-1,1[1]-binaphthyl 301
1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene 304
1,3-Dimesityl-1H-imidazolium Salts and 1,3-Dimesitylimidazolylidene 306
4-Dimethylaminopyridine 309
2,2-Dimethyl-1,3-dioxan-5-one 315
Dimethyldioxirane 320
(11bR)-4-(1,1-Dimethylethyl)-4,5-dihydro-3Hdinaphtho[2,1-c:1[1],2[1]- e]phosphepin 327
[4S-(4alpha,5alpha)]-1-(1,3-Dimethyl-2-oxido-4,5-diphenyl-1,3,2-diazaphospholidine-2-yl)piperidine 330
(1R,2S,4R,5S)-2,5-Dimethyl-7-phenyl-7-phosphabicyclo[2.2.1]heptane 334
1,4-Dimethyl-1H-1,2,4-triazol-4-ium Iodide 335
(11bR)-Dinaphtho[2,1-d:1[1],2[1]-f][1,3,2]dioxaphosphepin,2,6-Bis[3,5-bis (trifluoromethyl)phenyl]-4-hydroxy-,
4-Oxide 339
(11bR)-Dinaphtho[2,1-d:1[1],2[1]-f][1,3,2]dioxaphosphepin,4-Hydroxy-2,6-di-2-naphthalenyl-, 4-Oxide 343
Dinaphtho[2,1-d:1[1],2[1]-f][1,3,2]dioxaphosphepin,4-Hydroxy-2,6-diphenyl-,4-Oxide, (11bR)-(Family of Reagents) 345
5,6-Dioxaspiro[2.4]heptane-4,7-dione 351
2,2[1]-Diphenyl-[3,3[1]-biphenanthrene]-4,4[1]- diol (VAPOL) and 3,3[1]-Diphenyl-[2,2[1]- binaphthrene]-1,1[1]-diol(VANOL) 353
alpha, alpha-Diphenyl-2-pyrrolidinemethanol 365
Dispiro[2H-pyran-2,4[1]-[4H-5,6,8b]-triazaacenaphthylene-7[1](5[1]H),2[1][1]-[2H]- pyran], 1[1],2[1],2[1]a,3,3[1],3[1][1], 4,4[1][1],5,5[1][1],6,6[1][1],8[1],8[1]a-tetradecahydro-1[1],2[1]-dimethoxy-6, 6[1][1]-dimethyl-, monohydrochloride,(1[1]S,2R,2[1]S,2[1][1]R,2[1]aS,6S,6[1][1]S,8[1]aS)- 372
N-[(4-Dodecylphenyl)sulfonyl]-2-pyrrolidinecarboxamide(Hua Cat) 373
Dodecyl 4-[[[(2S)-2-pyrrolidinylcarbonyl]-amino]sulfonyl]benzoate(Hua Cat II) 376
(11bR)-4-Hydroxy-2,6-bis[2,4,6-tris-(1-methylethyl)phenyl]-dinaphtho[2,1-d:1[1],2[1]-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[1],2[1]-f][1,3,2]dioxaphosphepin-4-oxide, [(S)-TRIP] 379
N-[(1S)-1-(Hydroxydiphenylmethyl)-3-methylbutyl]-2-pyrrolidinecarboxamide 393
trans-4-Hydroxy-l-proline 395
(4aR,9aS)-4-Hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one 399
1H-Imidazolium, 1,3-Bis[2,6-bis-(1-methylethyl)phenyl],tetrafluoroborate(1-) 400
Iron(2+), tris(2,2[1]-bipyridine-N,N[1])-,Dibromide,(OC-6-11) 403
ß-Isocupreidine (ß-ICD) 406
1-Mesityl-3,4-dimethyl-4H-1,2,4-triazol-1-ium Tetrafluoroborate 411
9-Mesityl-10-methylacridinium Perchlorate 413
6[1]-Methoxy-(8S,9R)-cinchonan-9-yl N-tertbutoxycarbonyl-2-pyrrolidinecarboxylate 417
1-Methyl-2-azaadamantane N-Oxyl 420
(S)-1-Methyl-2-[(dihydroisoindol-2-yl)methyl]pyrrolidine 421
2-Methyltetrahydrofuran 422
Methyl(trifluoromethyl)dioxirane 428
Methyl Vinyl Ketone 438
d-2-Naphthylalanine, N,N[1]- [[(2S, 5S)-1-(4-pyridinyl)-2,5-pyrrolidinediyl]dicarbonyl]bis-, 3,3[1] - Dioctyl Ester1 and l-2-Naphthylalanine, N,N[1]-[[(2S,5S)-1-(4-pyridinyl)-2,5-pyrrolidinediyl]dicarbonyl]bis-, 3,3[1]-Dioctyl Ester 449
Nitroethane 451
4-Nitropyridine N-oxide 460
(2S)-N-(2,3,4,5,6-Pentafluorophenyl)-2-pyrrolidinecarboxamide 465
1,5-Pentanediamine, N,N[1]-Bis[(11bR)-3,5-dihydro-3,5-dimethyl-4-oxido-4H-dinaphtho[2,1-d:1[1],2[1]-f ]-[1,3,2]diazaphosphepin-4-yl]-N,N[1]-dimethyl 466
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]fluorine tetrafluoroborate; 6,7-Dihydro-2-phenyl-5-(phenylmethyl)-5H-pyrrolo[2,1-c]-1,2,4-triazolium chloride 474
(8alpha,9R)-(8[1][1]alpha,9[1][1]R)-1,1[1][1]-[1,3-Phenylenebis(methylene)]bis[9-hydroxy-cinchonanium]Dibromide and (9S)-(9[1][1]S)-1,1[1][1]-[1,3-Phenylenebis(methylene)]bis[9-hydroxy-cinchonanium]Dibromide 486
2-(Phenylmethoxy)acetaldehyde 489
(S)-Proline 494
(2S)-2-Pyrrolidinemethanol-alpha,alpha-bis(3,5-dimethylphenyl)and (2R)-2-Pyrrolidinemethanol-alpha, alpha-bis(3,5-dimethylphenyl) 517
1-(2-Pyrrolidinylmethyl)pyrrolidine 520
4-(1-Pyrrolidinyl)pyridine 525
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-) 528
Quinine 531
3-Quinuclidinol 547
Ruthenium (II), Tris(2,2[1]-bipyrazine-kappaN1, kappaN1[1]),1(OC-6-11)- 551
Ruthenium(II), Tris(2,2[1]-bipyridine-kappaN1,kappaN1[1])-,(OC-6-11)- 554
Ruthenium(II), Tris(1,10-phenanthroline-kappaN1,kappaN10)-,(OC-6-11)- 559
4,4[1]-Spirobi[4H-dinaphth[2,1-c:1[1],2[1]-e]-azepinium],3,3[1],5,5[1]-tetrahydro- 2,6-bis(3,4,5-trifluorophenyl), bromide 561
Spiro[6H-1,3-dioxolo[4,5-c]pyran-6,5[1]-oxazolidine]-3[1]-carboxylic acid, tetrahydro-2,2-dimethyl-2[1],7-dioxo-, 2-methyl-2-propyl ester, (3aR, 5[1]S, 7aR)- 567
Squaramide 571
Tetrachlorosilane 575
2,3,5,6-Tetrahydro-2,6-bis(phenylmethyl)-1H-imidazo[1,2-a] imidazole 582
2,2,6,6-Tetramethylpiperidin-1-oxyl 583
(S)-2-(5-1H-Tetrazolyl)pyrrolidine and (R)-2-(5-1H-Tetrazolyl)pyrrolidine 595
1,2,4-Triazolo[4,3-alpha]pyridinium, 5,6,7,8-tetrahydro-2-(2,3,4,5,6-pentafluorophenyl)-, Tetrafluoroborate 603
Triflimide 604
N-[4-(Trifluoromethyl)benzyl]-cinchoninium Bromide 612
3-(2,4,6-Trimethylphenyl)-1-methyl-1Hbenzo[d]imidazol-3-ium Iodide 614
(5S)-2,2,3-Trimethyl-5-(phenylmethyl)-4-imidazolidinone 616
1,5,7-Trimethyl-7-(5,6,7,8-tetrahydronaphth[2,3-d ]oxazol-2-yl)-3-azabicyclo-[3.3.1]nonan-2-one 621
2-Triphenylmethylpyrrolidine 624
Tris[(trifluoromethyl)sulfonyl]methane and Related Salts 625
l-Tryptophan, N,N[1]-[[(2S,5S)-1-(4-pyridinyl)-2,5-pyrrolidinediyl]-dicarbonyl]bis-, 3,3[1]-dioctyl Ester 628
Urea, N-[3,5-Bis(trifluoromethyl)phenyl]-N[1]-[(8a,9S)-6[1]-methoxycinchonan-9-yl]-; Urea, N-[3,5-Bis(trifluoromethyl)phenyl]-N[1]-(9R)-cinchonan-9-yl- 633
List of Contributors 639
Reagent Formula Index 655