Handbook of reagents for organic synthesis : reagents for organocatalysis / edited by Tomislav Rovis, Colorado State University, Fort Collins, CO, USA.

Format:

Book

Contributor:

Rovis, Tomislav, 1968- editor.

Language:

English

Subjects (All):

Organic compounds--Synthesis--Handbooks, manuals, etc.

Organic compounds.

Catalysis.

Chemical tests and reagents.

Physical Description:

1 online resource (1,937 pages) : illustrations

Edition:

1st ed.

Place of Publication:

Chichester, West Sussex : John Wiley & Sons, Incorporated, 2016.

Summary:

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.

Contents:

Handbook of Reagents for Organic Synthesis: Reagents for Organocatalysis

Contents

Preface

Introduction

Catalyst Finder

Recent Review Articles and Monographs

Short Note on InChIs and InChIKeys

A

4-Acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl

4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate

Original Commentary

First Update

Second Update

2'-Amino-[1,1'-binaphthalen]-2-ol

(9R)-9-Amino-9-deoxyquinidine

(9S)-Amino-9-deoxyquinine

(1R,2S)-1-Amino-2,3-dihydro-1H-inden-2-ol

(2S,4S)-2-(Anilinomethyl)-1-ethyl-4-hydroxypyrrolidine

(S)-2-(Anilinomethyl)pyrrolidine

9-Azabicyclo[3.3.1]nonane-N-oxyl

B

Benzoyl trimethylsilane

Benzyl 1,3-Butadiene-1-carbamate

3-Benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium Chloride

(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

3-Benzyl-4-methyl-1,3-thiazolium Chloride

cis-4-Benzyloxy-α,α-bis-(3,5-dimethylphenyl)-L-prolinol (2S,4R)-

N-Benzylquininium Chloride

3-Benzylthiazolium Bromide

Benzyltriethylammonium Chloride

Bicyclo[2.2.1]heptan-2-one, 7,7-Dimethyl-1-(1S,3S,4R)-2-thiabicyclo-[2.2.1]hept-3-yl-, (1S,4R)

[1,1'-Binaphthalene]-2,2'-diol, 3,3'-Bis [3,5-bis(trifluoromethyl)phenyl]-, (1R)-

N,N'-(1S)-[1,1'-Binaphthalene]-2,2'-diy lbis-(2S,2'S)-pyrrolidine-2-carboxamide

(R)-1,1'-Bi-2,2'-naphthol

Third Update

1,1'-Binaphthyl-2,2'-disulfonic Acid.

1,1'-Binaphthyl-2,2'-diyl Hydrogen Phosphate

N,N'-Bis[3,5-bis(trifluoromethyl)-phenyl]thiourea

1-[3,5-Bis(tert-butyl)phenyl]octahydro-3,6,6-trimethylcyclopenta[b]phosphole

1,3-bis(2,6-diisopropylphenyl)-4,5 dihydroimidazol-2-ylidene

1,3-Bis(2,6-diisopropylphenyl)imidazolidinium Chloride

1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene

(−)-(4R,5R)-4,5-Bis[hydroxy(diphenyl)-methyl]-2,2-dimethyl-1,3-dioxolane (TADDOL)

(2S,5S)-2-(Bis(4-methoxyphenyl)((trimethylsilyl)oxy)methyl)-5-(4-methoxy-3,5-dimethylphenyl)pyrrolidine

(3R,5R,8R)- 3,8-Bis(1-methylethyl)-2,2,7,7-tetrakis(4-methylphenyl)-1,4,6,9-tetraaza-5λ5-phosphaspiro[4,4]non-5-ene, Hydrochloride salt (1:1)

1,2-Bis(phenylsulfonyl)ethylene

3,3'-Bis(trifluoromethanesulfonyl)-2,2'-dihydroxy-1,1'-binaphthalene

1-[Bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene

3-[[3,5-Bis(trifluoromethyl)phenyl]-amino]-4-[[(1R,2R)-2-(dimethylamino)-cyclohexyl]amino]-3-cyclobutene-1,2-dione

N-[3,5-Bis(trifluoromethyl)phenyl]-N'-(9R)-cinchonan-9-yl-thiourea

N-[3,5-Bis(trifluoromethyl)phenyl]-N'-[(1R,2R)-2-(dimethylamino)cyclohexyl]-thiourea

1-[3,5-Bis(trifluoromethyl)phenyl]-3-{(2S)-3,3-dimethyl-1-[(triphenylphosphoranylidene)amino]butan-2-yl}thiourea

2-[Bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl]pyrrolidine

(1R)-3,3'-Bis(2,4,6-trimethylphenyl)-[1,1'-binaphthalene]-2,2'-dicarboxylic acid

Bromamine-T

Bromonitromethane

tert-Butyl 2-(tert-butyldimethylsilyl)-2-oxoacetate.

(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)

C

Chloramine-T

Cinchonanium, 1-(9-Anthracenylmethyl)-9-(propen-1-yloxy)-, Bromide (1:1), (8α,9R)

1,2-Cyclohexanediamine, N1,N2-Bis[4-(1-pyrrolidinyl)-2-quinolinyl]-, (1R,2R)-

D

1,4-Diazabicyclo[2.2.2]octane

1,3-Di-tert-butylimidazol-2-ylidene

Diethyl 1,4-Dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate

Diethyl Oxomalonate

1,3-Dihydro-1,3-bis(tricyclo[3.3.1.13,7] dec-1-yl)-2H-imidazol-2-ylidene

1,3-Dihydro-4,5-dimethyl-1,3-bis(1-methylethyl)-2H-imidazol-2-ylidene

4,5-Dihydro-4-phenyl-3H-dinaphtho[2,1-c:1',2'-e]phosphepin

2,3-Dihydro-2-phenylimidazo[2,1-b]benzothiazole

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

(R)-2,2'-Dihydroxy-3,3'diphenyl-1,1'-binaphthyl

1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene

1,3-Dimesityl-1H-imidazolium Salts and 1,3-Dimesityl-imidazolylidene

4-Dimethylaminopyridine

2,2-Dimethyl-1,3-dioxan-5-one

Dimethyldioxirane

(11bR)-4-(1,1-Dimethylethyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]phosphepin

[4S-(4α,5α)]-1-(1,3-Dimethyl-2-oxido-4,5-diphenyl-1,3,2-diazaphospholidine-2-yl)piperidine

(1R,2S,4R,5S)-2,5-Dimethyl-7-phenyl-7-phosphabicyclo[2.2.1]heptane

1,4-Dimethyl-1H-1,2,4-triazol-4-ium Iodide

(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.

(11bR)-Dinaphtho[2,1-d:1',2'-f][1,3,2] dioxaphosphepin, 4-Hydroxy-2,6-di-2-naphthalenyl-, 4-Oxide

Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 4-Hydroxy-2,6-diphenyl-, 4-Oxide, (11bR)- (Family of Reagents)

5,6-Dioxaspiro[2.4]heptane-4,7-dione

2,2'-Diphenyl-[3,3'-biphenanthrene]-4,4'-diol (VAPOL) and 3,3'-Diphenyl-[2,2'-binaphthrene]-1,1'-diol (VANOL)

α,α-Diphenyl-2-pyrrolidinemethanol

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)-

N-[(4-Dodecylphenyl)sulfonyl]-2-pyrrolidinecarboxamide (Hua Cat)

Dodecyl 4-[[[(2S)-2-pyrrolidinylcarbonyl]- amino]sulfonyl]benzoate (Hua Cat II)

H

(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] &amp

(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

trans-4-Hydroxy-L-proline

(4aR,9aS)-4-Hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one

1H-Imidazolium, 1,3-Bis[2,6-bis-(1-methylethyl)phenyl], tetrafluoroborate(1-)

I

Iron(2+), tris(2,2'-bipyridine-N,N')-, Dibromide, (OC-6-11)

β-Isocupreidine (β-ICD)

M

1-Mesityl-3,4-dimethyl-4H-1,2,4-triazol-1-ium Tetrafluoroborate

9-Mesityl-10-methylacridinium Perchlorate

6'-Methoxy-(8S,9R)-cinchonan-9-yl-N-tert-butoxycarbonyl-2-pyrrolidinecarboxylate

1-Methyl-2-azaadamantane N-Oxyl

(S)-1-Methyl-2-[(dihydroisoindol-2-yl)methyl]pyrrolidine.

2-Methyltetrahydrofuran

Methyl(trifluoromethyl)dioxirane

Methyl Vinyl Ketone

N

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

Nitroethane

4-Nitropyridine N-oxide

P

(2S)-N-(2,3,4,5,6-Pentafluorophenyl)-2-pyrrolidinecarboxamide

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

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

(8α,9R)-(8''α,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

2-(Phenylmethoxy)acetaldehyde

(S)-Proline

(2S)-2-Pyrrolidinemethanol-α,α-bis(3,5-dimethylphenyl) and (2R)-2-Pyrrolidinemethanol-α, α-bis(3,5-dimethylphenyl)

1-(2-Pyrrolidinylmethyl)pyrrolidine

4-(1-Pyrrolidinyl)pyridine

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-)

Q

Quinine

3-Quinuclidino

R

Ruthenium (II), Tris(2,2'-bipyrazine-κN1,κN1'), (OC-6-11).

Ruthenium(II), Tris(2,2'-bipyridine-κN1,κN1')-, (OC-6-11).

Notes:

Includes bibliographical references and index.

Description based on print version record.

ISBN:

1-119-06102-4

OCLC:

960819895