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El. knyga: Handbook of Reagents for Organic Synthesis: Reagents for Organocatalysis

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  • Formatas: EPUB+DRM
  • Išleidimo metai: 14-Sep-2016
  • Leidėjas: John Wiley & Sons Inc
  • Kalba: eng
  • ISBN-13: 9781119061021
Kitos knygos pagal šią temą:
Handbook of Reagents for Organic Synthesis: Reagents for OrganocatalysisDidesnis paveikslėlis
  • Formatas: EPUB+DRM
  • Išleidimo metai: 14-Sep-2016
  • Leidėjas: John Wiley & Sons Inc
  • Kalba: eng
  • ISBN-13: 9781119061021
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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.

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.
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(1)
4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate
2(11)
2'-Amino-[ 1, 1'-binaphthalen]-2-ol
13(3)
(9R)-9-Amino-9-deoxyquinidine
16(8)
9(S)-Amino-9-deoxyquinine
24(11)
(1R, 2S)-1-Amino-2,3-dihydro-1 H-inden-2-ol
35(15)
(2S,4S)-2-(Anilinomethyl)-1-ethyl-4-hydroxypyrrolidine
50(1)
(S)-2-(Anilinomethyl)pyrrolidine
51(8)
9-Azabicyclo[ 3.3.1]nonane-N-oxyl
59(2)
Benzoyl trimethylsilane
61(5)
Benzyl 1,3-B utadiene-1-carbamate
66(3)
3-Benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium Chloride
69(3)
(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)
3-Benzyl-4-methyl-1,3-thiazolium Chloride
75(1)
Cis-4-Benzyloxy-α, α-bis-(3,5-dimethylphienyl)-L-prolinol (2S,4R)
76(2)
N-Benzylquininium Chloride
78(7)
3-Benzylthiazolium Bromide
85(1)
Benzyltriethylammonium Chloride
86(2)
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(7)
[ 1,1'-Binaphthalene]-2,2'-diol, 3,3'-Bis [ 3,5-bis(trifluoromethyl)phenyl]-, (1R)-
95(3)
N, N'-(1S)-[ 1, 1'-Binaphthalene]-2,2'-diy lbis-(25,2S)-pyrrolidine-2-carboxamide
98(3)
(R)-1,1'-Bi-2,2'-naphthol
101(23)
1, 1'-Binaphthyl-2,2'-disulforiic Acid
124(5)
1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate
129(4)
N,N'-Bis[ 3.5-bisitrifluoromethyl)-phenyl] thiourea
133(4)
1-[ 3,5-Bis(tert-butyl)phenyl]octahydro-3,6,6-trimethylcyclopenta[ b]phosphole
137(2)
1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene
139(7)
1,3-Bis(2,6-diisopropylphenyl)imidazolidinium Chloride
146(3)
1,3- Bis(2,6-diisopropylphenyl)imidazol-2-ylidene
149(3)
(-)-(4R,5R)-4,5-Bis[ hydroxy(diphenyl)-methyl]-2,2-dimethyl-1,3-dioxolane(TADDOL)
152(9)
(2S,5S)-2-(Bis(4-methoxyphenyl)((trimethylsilyl)oxy) methyl)-5-(4-rnethoxy-3,5-dimethylphenyl)pyrrolidine
161(1)
(3R,5R,8R)-3,8-Bis(1-niethylethyl)-2,2,7,7-tetrakis(4-methylphenyl)-1,4,6,9-tetraaza-5λ5-phosphaspiro[ 4,4] non-5-ene, Hydrochloride salt (1:1)
162(1)
1,2-Bis(phenylsulfonyl)ethylene
163(9)
3,3'-Bis(trifluoromethanesulfonyl)-2,2'-dihydroxy-1,1'-binaphthalene
172(2)
1-[ Bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene
174(6)
3-[ [ 3,5-B is(trifluoromethyl)phenyl]-amino]-4-[ [ (1 R,2R)-2-(dimethylamino)-cyclohexyl]amino]-3-cyclobutene-1,2-dione
180(3)
N-[ 3,5-Bis(trifluoromethyl)phenyl]-N'-(9R)-cinchonan-9-yl-thiourea
183(3)
N-[ 3,5-Bis(trifluoromethyl)phenyl]-N'-[ (1R,2R)-2-(dimethylamino)cyclohexyl]-thiourea
186(3)
1-[ 3,5-Bis(trifluoromethyl)phenyl]-3-{(2S)-3,3-dimethyl-1-[ (triphenylphosphoranylidene)arnino] butan-2-yl}thiourea
189(3)
2- [ Bis[ 3,5-bis(trifluoromethyl)phenyl][ (trimethylsilyl) oxy]methyl]pyrrolidine
192(7)
(1R)-3,3'-Bis(2,4,6-trimcthylphenyl)-[ 1,1'-binaphthalene]-2,2'-dicarboxylic acid
199(3)
Bromamine-T
202(3)
Bromonitromethane
205(5)
Tert-Butyl2-(teri-butyldimethylsilyl)-2-oxoacetate
210(4)
(S)-5-((tert-Buryldimethylsilyloxy)-diphenylmethyl)-2-phenyl-6 7-dihyoro-5H-pyrrolo[ 2,1-c] [ 1,2,4]triazol-2-ium Tetrafluoroborate la (and Related Reagents)
214(5)
Chloramine-T
219(8)
Cinchonanium, 1-(9-Anthracenylmethyl)-9-(propen-1-yloxy)-, Bromide(1:1), (8α,9R)
227(8)
1,2-Cyclohexanediamine, N', N2-Bis[ 4-(1-pyrrolidinyl) 2-quinolinyl]-, (1R,2R)-
235(6)
1,4-Diazahicyclo[ 2.2.2]octane
241(6)
13-Di-tert-butylirnidazo1-2-yLidene
247(7)
Diethyl 1,4-Dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
254(7)
Diethyl Oxomalonate
261(9)
1,3-Dihydro-1,3-bis(tricyclo[ 3.3.1.13,7]dec-1-yl) 2H-imidazol-2-ylidene
270(3)
1,3-Dihydro-4,5-dimethyl-1,3-bis(1-methylethyl)-2H-imiduzol-2-ylidene
273(4)
4,5-Dihydro-4-phenyl-3H-dinaphtho[ 2,1-c:1';2'-e]phosphepin
277(3)
2,3-Dihydro-2-phenylimidazo[ 2,1-b]benzothiazole
280(6)
6,7-Dihydro-2-phenyl-5-(phenylmethyl)-5H-pyrrolo[ 2,1 -c]-1,2,4-triazolium Chloride
286(15)
(R)-2,2'-Dihydroxy-3,3' diphenyl-1,1-binaphthyl
301(3)
1,3-Dimesityl-4,5-dihydroirnidazol-2-ylidene
304(2)
1,3- Dimesityl-1H-irrjidazoliumSalts and 1,3-Dirnesityl-irnidazolylidene
306(3)
4-Dimethy laminopyridine
309(6)
2,2-Dimethyl-1,3-dioxan-5-one
315(5)
Dimethyldioxirane
320(7)
(11bR)-4-(1,1-Dimethylethyl)-4,5-dihydro-3H-dinaphtho[ 2,1-c: 1 2-e]phosphepin
327(3)
[ 45-(4α, 5α)]-1-(1,3-Dimethyl-2-oxido-4,5-diphenyl-1,3,2-diazaphospholidine-2-yl)piperidine
330(4)
(1R,2S,4R,5S)-2,5-Dimethyl-7-phenyl-7-phosphabicyclo [ 2.2.1]heptane
334(1)
1.4-Dimethyl-1H-1,2,4-triazol-4-ium Iodide
335(4)
(11 bR)-Dinaphtho[ 2,1-d:1', 2'-f][ 1,3,2]dioxaphosphepin, 2,6-Bis[ 3,5-bis (trifluoromethyl)phenyl]-4-hydroxy-,4-Oxide
339(4)
(11 bR)-Dinaphtho[ 2,1-d:1,2'-f] [ 1,3,2]dioxaphosphepin, 4-Hydroxy-2,6-di-2-naphthalenyl-,4-Oxide
343(2)
(11 bR)-Dinaphtho[ 2, 1-d:1',2'-f][ 1,3,2]dioxaphosphepin, 4-Hydroxy-2,6-diphenyl-,4-Oxide, (11 bR)-(Family of Reagents)
345(6)
5,6- Dioxaspiro[ 2.4]heptane-4,7-dione
351(2)
2,2'-Diphenyl-[ 3,3'-biphenanthrene]-4,4'- diol (VAPOL) and 3,3'-Dipheny]-[ 2,2'- binaphthrene]-1,1'-diol (VANOL)
353(12)
α, α-Diphenyl-2-pyrrolidinemethanol
365(7)
Dispiro [ 2H-pyran-2,4- [ 4H-5,6,8b] -triazaacenaphthylene-7'(5H)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, (1'5,2R,2S,2"/R,2'aS, 6S,6S,8'a5)-
372(1)
N-[ (4-Dodecylphenyl)sulfonyl]-2-pyrrolidine-carboxarnide (Hua Cat)
373(3)
Dodecyl 4-[ [ [ (2S)-2-pyrrolidinylcarbonyl]-amino] sulfonyl]benzoate(Hua Cat II)
376(3)
(11 bR)-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]
379(14)
N-[ (1S-1-(Hydroxydiphenylmethyl)-3-memylbutyl]-2-pyirolidmecarboxamide
393(2)
Trans-4-Hydroxy-l-proline
395(4)
(4aR, 9ay)-4-Hydroxy-4,4a,9,9a-tetrahydroindeno [ 2,1-b][ 1,4]oxazin-3(2H)-one
399(1)
1H-Imidazolium, 1,3-Bis[ 2,6-bis-(1-methylethyl) phenyl], tetrafluoroborate(1-)
400(3)
Iron(2+-), tris(2;2'-bipyridine-A, N')-, Dibromide, (OC-6-11)
403(3)
β-Isocupreidine (β-ICD)
406(5)
1-Mesityl-3,4-dimethy 1-4H-1,2,4-triazol-1-ium Tetrafluoroborate
411(2)
9-Mesityl-10-methylacridinium Perchlorate
413(4)
6'-Methoxy-(85, 9R)-cinchonan-9-yl N-tert-butoxycarbonyl-2-pyrrolidinecarboxylate
417(3)
1- Methyl-2-azaadaniantane N-Oxyl
420(1)
(S)-1-Methy 1-2-[ (dihydroisoindol-2-yl)methyl] pyrrolidine
421(1)
2-Methyltetrahydrofuran
422(6)
Methyl(trifluoromethyl)dioxirane
428(10)
Methyl Vinyl Ketone
438(11)
D-2-Naphthylalanine, N,N'-[ [ (2S, 5S)-1-(4-pyridinyl)-2,5-pyrrolidinediyl]dicarbonyl]bis-, 3,3' - Dioctyl Ester1 and L-2-Naphthylalanine, N,N'-[ [ (2S,5S)-1-(4-pyridinyl)-2,5-pyrrolidinediyl]dicarbonyl]bis-, 3,3'-Dioctyl Ester
449(2)
Nitroethane
451(9)
4-Nitropyridine N-oxide
460(5)
(2S)-N-(2,3,4,5,6-Pentafluorophenyr)-2-pyrrolidinecarboxamide
465(1)
1,5-Pentanediamine, N,N'-Bis[ 11 bR)-3,5-dihydro-3,5-dimethyl-4-ox ido-4H-dinaphtho [ 2,1 -d:1',2'-f]-[ 1,3,2]diazaphosphepin-4-yl]-N,N'-dimethyl
466(8)
2-Pheny 1-6,10b-dihydro-4H,5aH-5-oxa-3,10c-diaza-2-azonia-cyelopenta[ c] fluorene tetrafluoroborate; 2-Pentafluorophenyl-6,10b-dihydro-4H, 5aH-5-oxa-3,10c-diaza-2-azoniacyclopenta[ c]fluorene tetrafluoroborate; 6,7-Dihydro-2-phenyl-5-(phenylmethyl)-5H-pyrrolo[ 2,1-c] -1,2,4-triazolium chloride
474(12)
(8α,9R)-(8" α, 9"R)-1,1"-[ 1,3-Phenylenebis(methylene)]bis[ 9-hydroxy-cinchonanium] Dibromide and (95)-(9"5)-1,1"-[ 1,3-Phenylenebis(methylene)]bis[ 9-hydroxy-cinchonanium] Dibromide
486(3)
2-(Phenylmethoxy)acetaldehyde
489(5)
(S)-Proline
494(23)
(2S)-2-Pyrrolidinemethanol-α, α bis(3,5-dimethylphenyl) and (2R)-2-Pyrrolidinemethanol-α, α-bis(3,5-dimethylphenyl)
517(3)
1-(2-Pyrrolidinylmethyl)pyrrolidine
520(5)
4-(1-Pyrro]idinyl)pyridine
525(3)
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(3)
Quinine
531(16)
3- Quinuclidinol
547(4)
Ruthenium (II), Tris(2,2'-bipyrazine-κN1, κN1'),1 (OC-6-11)-
551(3)
Ruthenium(II), Tris(2,2'-bipyridine-κN1, κN1')-, (OC-6-11)-
554(5)
Ruthenium(H), Tris(1,1O-phenanthroline-κN1, κN10)-(OC-6-11)-
559(2)
4,4'-Spirobi[ 4W-dinaphth[ 2,1-c:1'2'-e]-azepinium], 3,3'5,5'-tetrahydro-2,6-bis(3,4,5-trifluorophenyl), bromide
561(1)
Spiro [ 6H-1,3-dioxolo [ 4,5-c]pyran-6,5'-oxazolidirie]-3'-carboxylic acid, tetrahydro-2,2-dimethyl-2', 7-dioxo-, 2-methyl-2-propyl ester, (3aR, 5S, 7aR)-
561(10)
Squaramide
571(4)
Tetrachlorosilane
575(7)
2,3,5,6-Tetrahydro-2,6-bis(phenylmethyl)-1H-imidazo[ 1,2-a] imidazole
582(1)
2,2,6,6-Tetramethylpiperidin- 1-oxyl
583(12)
(S)-2-(5-H-Tetrazolyl)pyrrolidine and (R)-2-(5-1H-Tetrazolyl)pyrrolidine
595(8)
1,2,4-Triazolo[ 4,3-α]pyridinium, 5,6,7,8-tetrahydro-2-(2,3,4,5,6-pentafluorophenyl)-, Tetrafluoroborate
603(1)
Triflimide
604(8)
N-[ 4-(Trifluoromethyl)benzyl]-cinchoninium Bromide
612(2)
3-(2,4,6-Trimethylphenyl)-1 -methyl-1H-benzo[ d)imidazol-3-ium Iodide
614(2)
(5S')-2,2,3-Trimethyl-5-(phenylmethyl)-4-imidazolidinone
616(5)
1,5,7-Trimethyl-7-(5,6,7,8-tetrahydro-naphth[ 2,3-d]loxazol-2-yl)-3-azabicyclo-[ 3.3.1]nonan-2-one
621(3)
2-Triphenylmethylpyrrolidine
624(1)
Tris[ (trifluoromethy)sulfonyl]methane and Related Salts
625(3)
L-Tryptophan, N,N'-[ [ (2S,5S)-1-(4-pyridinyl)-2,5-pyrrolidinediyl]-dicarbonyl]bis-, 3,3'-dioctyl Ester
628(5)
Urea, N-[ 3,5-Bis(trirluoroniethyl)phenyl]-N-[ (8a,9S)-6'-methoxycinchonan-9-yl]-; Urea, N-[ 3,5-Bis(trifluoromethyl)phenyl]-N-(9R)-cinchonan-9-yl-
633(6)
List of Contributors 639(16)
Reagent Formula Index 655(4)
Subject Index 659
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.
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