Handbook of Reagents for Organic Synthesis (eBook)

Reagents for Organocatalysis

Tomislav Rovis (Herausgeber)

eBook Download: EPUB

2016
John Wiley & Sons (Verlag)
9781119061021 (ISBN)

Infos

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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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.

Autor

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.

Textauszug

Catalyst Finder

What follows is a compilation of the catalysts in this volume, grouped by type. We begin with achiral catalysts of all reaction families and then delineate chiral, single enantiomer catalysts by reactant type.

Achiral

1. 4-Acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl
2. 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate
3. 9-Azabicyclo[3.3.1]nonane-N-oxyl
4. 3-Benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium Chloride
5. 3-Benzyl-4-methyl-1,3-thiazolium Chloride
6. 3-Benzylthiazolium Bromide
7. Benzyltriethylammonium Chloride
8. N,N′-Bis[3,5-bis(trifluoromethyl)-phenyl]thiourea
9. 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene
10. 1,3-Bis(2,6-diisopropylphenyl)imidazolidinium Chloride
11. 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene
12. 1-[Bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene
13. 1,4-Diazabicyclo[2.2.2]octane
14. 1,3-Di-tert-butylimidazol-2-ylidene
15. 1,3-Dihydro-1,3-bis(tricyclo[3.3.1.13,7]dec-1-yl)-2H-imidazol-2-ylidene
16. 1,3-Dihydro-4,5-dimethyl-1,3-bis(1-methylethyl)-2H-imidazol-2-ylidene
17. 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene
18. 1,3-Dimesityl-1H-imidazolium Salts and 1,3-Dimesityl-imidazolylidene
19. 4-Dimethylaminopyridine
20. 1,4-Dimethyl-1H-1,2,4-triazol-4-ium Iodide
21. 1H-Imidazolium, 1,3-Bis[2,6-bis-(1-methylethyl)phenyl], tetrafluoroborate(1-)
22. Iron(2+), tris(2,2′-bipyridine-N,N′)-, dibromide, (OC-6-11)
23. 1-Mesityl-3,4-dimethyl-4H-1,2,4-triazol-1-ium Tetrafluoroborate
24. 9-Mesityl-10-methylacridinium Perchlorate
25. 1-Methyl-2-azaadamantane N-Oxyl
26. 4-(1-Pyrrolidinyl)pyridine
27. Ruthenium(II), Tris(2,2′-bipyrazine-κN1, κN1′),1 (OC-6-11)-
28. Ruthenium(II), Tris(2,2′-bipyridine-κN1,κN1′)-, (OC-6-11)-
29. Ruthenium(II), Tris(1,10-phenanthroline-κN1,κN10)-, (OC-6-11)-
30. Squaramide
31. 2,2,6,6-Tetramethylpiperidin-1-oxyl
32. 1,2,4-Triazolo[4,3-α]pyridinium, 5,6,7,8-tetrahydro-2-(2,3,4,5,6-pentafluorophenyl)-, tetrafluoroborate(1-) (1:1)
33. Triflimide
34. 3-(2,4,6-Trimethylphenyl)-1-methyl-1H-benzo[d]imidazol-3-ium Iodide
35. Tris[(trifluoromethyl)sulfonyl]methane and Related Salts

Amine

1. (9R)-9-Amino-9-deoxyquinidine
2. 9(S)-Amino-9-deoxyquinine
3. (1R,2S)-1-Amino-2,3-dihydro-1H-inden-2-ol
4. (2S,4S)-2-(Anilinomethyl)-1-ethyl-4-hydroxypyrrolidine
5. (S)-2-(Anilinomethyl)pyrrolidine
6. cis-4-Benzyloxy-α,α-bis-(3,5-dimethylphenyl)-L-prolinol (2S,4R)-
7. N,N′-(1S)-[1,1′-Binaphthalene]-2,2′-diylbis-(2S,2′S)-pyrrolidine-2-carboxamide
8. (2S,5S)-2-(Bis(4-methoxyphenyl)((trimethylsilyl)oxy)methyl)-5-(4-methoxy-3,5-dimethylphenyl)pyrrolidine
9. 2-[Bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl]pyrrolidine
10. α,α-Diphenyl-2-pyrrolidinemethanol
11. N-[(4-Dodecylphenyl)sulfonyl]-2-pyrrolidinecarboxamide (Hua Cat)
12. Dodecyl 4-[[[(2S)-2-pyrrolidinylcarbonyl]-amino]sulfonyl]benzoate (Hua Cat II)
13. N-[(1S)-1-(Hydroxydiphenylmethyl)-3-methylbutyl]-2-pyrrolidinecarboxamide
14. trans-4-Hydroxy-l-proline
15. (S)-1-Methyl-2-[(dihydroisoindol-2-yl)methyl]pyrrolidine
16. (2S)-N-(2,3,4,5,6-Pentafluorophenyl)-2-pyrrolidinecarboxamide
17. (S)-Proline
18. (2S)-2-Pyrrolidinemethanol-α,α-bis(3,5-dimethylphenyl) and (2R)-2-Pyrrolidinemethanol-α,α-bis(3,5- dimethylphenyl)
19. 1-(2-Pyrrolidinylmethyl)pyrrolidine
20. (S)-2-(5-1H-Tetrazolyl)pyrrolidine and (R)-2-(5-1H-Tetrazolyl)pyrrolidine
21. (5S)-2,2,3-Trimethyl-5-(phenylmethyl)-4-imidazolidinone
22. 2-Triphenylmethylpyrrolidine

Brønsted Acid

1. 1,1′-Binaphthyl-2,2′-disulfonic Acid
2. 1,1′-Binaphthyl-2,2′-diyl Hydrogen Phosphate
3. (1R)-3,3′-Bis(2,4,6-trimethylphenyl)-[1,1′-binaphthalene]-2,2′-dicarboxylic acid
4. (11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin, 2,6-Bis[3,5-bis(trifluoromethyl)phenyl]-4-hydroxy-, 4-Oxide
5. (11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin, 4-Hydroxy-2,6-di-2-naphthalenyl-, 4-Oxide
6. Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin, 4-Hydroxy-2,6-diphenyl-, 4-Oxide, (11bR)- (Family of Reagents)
7. (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]

Chiral Ketone

1. 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)-

Hydrogen Bond

1. 2′-Amino-[1,1′-binaphthalen]-2-ol
2. [1,1′-Binaphthalene]-2,2′-diol, 3,3′-Bis[3,5-bis(trifluoromethyl)phenyl]-,(1R)-
3. (R)-1,1′-Bi-2,2′-naphthol
4. (–)-(4R,5R)-4,5-Bis[hydroxy(diphenyl)-methyl]-2,2-dimethyl-1,3-dioxolane (TADDOL)
5. 3,3′-Bis(trifluoromethanesulfonyl)-2,2′-dihydroxy-1,1′-binaphthalene
6. 3-[[3,5-Bis(trifluoromethyl)phenyl]-amino]-4-[[(1R,2R)-2-(dimethylamino)-cyclohexyl]amino]-3-cyclobutene-1,2-dione
7. N-[3,5-Bis(trifluoromethyl)phenyl]-N′-(9R)-cinchonan-9-yl-thiourea
8. N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(1R,2R)-2-(dimethylamino)cyclohexyl]-thiourea
9. 1-[3,5-Bis(trifluoromethyl)phenyl]-3-{(2S)-3,3-dimethyl-1-[(triphenylphosphoranylidene)amino]butan-2-yl}thiourea
10. (R)-2,2′-Dihydroxy-3,3′diphenyl-1,1′-binaphthyl
11. 2,2′-Diphenyl-[3,3′-biphenanthrene]-4,4′-diol (VAPOL) and 3,3′-Diphenyl-[2,2′-binaphthrene]-1,1_-diol (VANOL)
12. 1,5,7-Trimethyl-7-(5,6,7,8-tetrahydronaphth[2,3-d ]oxazol-2-yl)-3-azabicyclo-[3.3.1]nonan-2-one
13. Urea, N-[3,5-bis(trifluoromethyl)phenyl]-N′-[(8α,9S)-6′-methoxycinchonan-9-yl]-; Urea, N-[3,5-bis(trifluoromethyl)phenyl]-N′-(9R)-cinchonan-9-yl-

Lewis Base

1. Bicyclo[2.2.1]heptan-2-one, 7,7-Dimethyl-1-(1S,3S,4R)-2-thiabicyclo-[2.2.1]hept-3-yl-, (1S,4R)
2. 1,2-Cyclohexanediamine, N1,N2-Bis[4-(1-pyrrolidinyl)-2-quinolinyl]-, (1R,2R)-
3. 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)-
4. β-Isocupreidine (β-ICD)
5. 6′-Methoxy-(8S,9R)-cinchonan-9-yl N-tert-butoxycarbonyl-2-pyrrolidinecarboxylate
6. 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
7. 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
8. Quinine
9. 3-Quinuclidinol
10. 2,3,5,6-Tetrahydro-2,6-bis(phenylmethyl)-1H-imidazo[1,2-a]-imidazole
11. l-Tryptophan, N,N′-[[(2S,5S)-1-(4-pyridinyl)-2,5-pyrrolidinediyl]dicarbonyl]-bis-, 3,3′-dioctyl Ester

N-Heterocyclic Carbene (NHC)

1. (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
2. (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)
3. 6,7-Dihydro-2-phenyl-5-(phenylmethyl)-5H-pyrrolo[2,1-c]-1,2,4-triazolium Chloride
4. 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; 6,7-Dihydro-2-phenyl-5-(phenylmethyl)-5H-pyrrolo[2,1-c]-1,2,4-triazolium chloride
5. 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)-,...

Produkt-Details

• Erscheint lt. Verlag: 14.9.2016
• Sprache: englisch
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Themenwelt: Naturwissenschaften ► Chemie ► Physikalische Chemie
• Themenwelt: Technik
• Schlagworte: Amino • anilinomethyl • azabicyclo • binaphthalen • catalyst • Chemie • Chemistry • deoxyquinidine • deoxyquinine • dihydro • ethyl hydroxypyrrolidine • Finder • inchis • Introduction • Methods - Synthesis & Techniques • 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: 9781119061021 / 9781119061021