Shinji Tanaka

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Organization: Nagoya University , Japan

Department: Graduate School of Pharmaceutical Sciences

Title: Assistant Professor(PhD)

Chemicals
References

Recent topics in catalytic asymmetric hydrogenation of ketones

Co-reporter:Masahiro Yoshimura, Shinji Tanaka, Masato Kitamura

Tetrahedron Letters 2014 Volume 55(Issue 27) pp:3635-3640

Publication Date(Web):2 July 2014

DOI:10.1016/j.tetlet.2014.04.129

Asymmetric hydrogenation of ketones (AHK) was revolutionized in 1987 and again in 1995 when Ru(CH3COO)2(binap)/HCl and RuCl2(binap)/diamine, respectively, were developed. Since then, the number of reports on Ru-catalyzed AHK has increased exponentially, and the utility of other precious metals (Os, Rh, Ir, and Pd) has also been shown. The utilization of inexpensive base metals (Fe, Co, Ni, and Cu) has been a recent trend. This digest summarizes the key advances in AHK in the past decade by categorizing the chiral ligands into six types: (i) diphosphines, (ii) diphosphines/diamines, (iii) tridentate or tetradentate phosphine amines, (iv) diamines, (v) tetradentate amines, and (vi) tetradentate thioether amines.Figure optionsDownload full-size imageDownload high-quality image (67 K)Download as PowerPoint slide

Pentanoic acid, 3-hydroxy-4,4-dimethyl-, methyl ester, (R)-

CAS:87319-80-0

Pentanoic acid, 3-hydroxy-4,4-dimethyl-, methyl ester, (R)-

2H-Pyran-2-one, 6-ethenyltetrahydro-, (6S)-

CAS:879880-52-1

2H-Pyran-2-one, 6-ethenyltetrahydro-, (6S)-

CAS:87898-91-7

Pentanamide, N,N,4,4-tetramethyl-3-oxo-

CAS:187742-81-0

CAS:906373-47-5

CAS:906373-46-4

CAS:1533410-76-2

CAS:906373-48-6

CAS:906373-44-2

CAS:906373-41-9

CAS:906373-42-0

CAS:1533410-77-3

CAS:81925-29-3

2-Propen-1-ol, 3-(tributylstannyl)-

CAS:91199-39-2

2(3H)-Furanone, 5-ethenyldihydro-, (S)-

4-Hexenoic acid, 6-hydroxy-, methyl ester, (4Z)-

CAS:699001-96-2

4-Hexenoic acid, 6-hydroxy-, methyl ester, (4Z)-

2-Propenoic acid, 3-(2-iodophenyl)-, ethyl ester, (2E)-

CAS:378759-67-2

2-Propenoic acid, 3-(2-iodophenyl)-, ethyl ester, (2E)-

2-Butanol, 1-(dimethylamino)-3,3-dimethyl-, (R)-

CAS:128821-03-4

2-Butanol, 1-(dimethylamino)-3,3-dimethyl-, (R)-

CAS:40238-88-8

3-Undecanone, 2,2-dimethyl-

CAS:81677-42-1

5-Heptenoic acid, 7-hydroxy-, (E)-

Carbamic acid, (2-phenylethyl)-, 2-propenyl ester

CAS:70867-37-7

Carbamic acid, (2-phenylethyl)-, 2-propenyl ester

Pentanamide, 3-hydroxy-N,N,4,4-tetramethyl-, (S)-

CAS:89209-19-8

Pentanamide, 3-hydroxy-N,N,4,4-tetramethyl-, (S)-

1H-2-Benzopyran-1-one, 3-ethenyl-3,4-dihydro-

CAS:90992-06-6

1H-2-Benzopyran-1-one, 3-ethenyl-3,4-dihydro-

Propanedioic acid, [(2E)-4-hydroxy-3-methyl-2-butenyl]-, dimethyl ester

CAS:448297-52-7

Propanedioic acid, [(2E)-4-hydroxy-3-methyl-2-butenyl]-, dimethyl ester

2,4-Pentanediol, 3,3-dimethyl-, (R*,S*)-

CAS:25140-14-1

2,4-Pentanediol, 3,3-dimethyl-, (R*,S*)-

Pentanoic acid, 3-hydroxy-4,4-dimethyl-, methyl ester, (S)-

CAS:124573-30-4

Pentanoic acid, 3-hydroxy-4,4-dimethyl-, methyl ester, (S)-

CAS:133942-70-8

2-Hexen-1-ol, 6-iodo-, (2E)-

2-Pentenoic acid, 3-methyl-5-phenyl-, methyl ester, (E)-

CAS:107647-43-8

2-Pentenoic acid, 3-methyl-5-phenyl-, methyl ester, (E)-

2-Butanol, 1-(dimethylamino)-3,3-dimethyl-, (±)-

CAS:117064-17-2

2-Butanol, 1-(dimethylamino)-3,3-dimethyl-, (±)-

CAS:56860-50-5

2-BUTANOL, 1-(DIMETHYLAMINO)-3,3-DIMETHYL-, (S)-

2-Pentenoic acid, 4-methyl-3-phenyl-, methyl ester, (2E)-

CAS:157031-64-6

2-Pentenoic acid, 4-methyl-3-phenyl-, methyl ester, (2E)-

Cyclopentanol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, trans-

CAS:149357-69-7

Cyclopentanol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, trans-

CAS:83285-42-1

1(3H)-ISOBENZOFURANONE, 3-ETHENYL-

Ethyl 3-(tert-butyldimethylsiloxy)-3-phenylpropionate

CAS:57956-47-5

Ethyl 3-(tert-butyldimethylsiloxy)-3-phenylpropionate

L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-seryl-,1,1-dimethylethyl ester

CAS:704910-26-9

L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-seryl-,1,1-dimethylethyl ester

L-Phenylalanine,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-2-propenyl-L-seryl-,1,1-dimethylethyl ester

CAS:704910-22-5

L-Phenylalanine,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-2-propenyl-L-seryl-,1,1-dimethylethyl ester

Benzene, [[[(1R,2R)-2-(2-propenyloxy)cyclopentyl]oxy]methyl]-, rel-

CAS:704910-19-0

Benzene, [[[(1R,2R)-2-(2-propenyloxy)cyclopentyl]oxy]methyl]-, rel-

CAS:545377-20-6

3-UNDECANOL, 2,2-DIMETHYL-, (3S)-

CAS:320381-26-8

(2-phenylnaphthalen-1-yl)boronic acid

CAS:857678-57-0

3-Undecanol, 2,2-dimethyl-, (3R)-

Benzenepropanoic acid, b-(acetylamino)-, ethyl ester

CAS:7554-23-6

Benzenepropanoic acid, b-(acetylamino)-, ethyl ester

Cyclopentane, 1-(methoxymethoxy)-2-(2-propenyloxy)-, (1R,2R)-rel-

CAS:704910-20-3

Cyclopentane, 1-(methoxymethoxy)-2-(2-propenyloxy)-, (1R,2R)-rel-

CAS:18992-89-7

prop-2-en-1-yl phenylcarbamate

Cyclopentanol, 2-(2-propenyloxy)-, benzoate, (1R,2R)-rel-

CAS:704910-18-9

Cyclopentanol, 2-(2-propenyloxy)-, benzoate, (1R,2R)-rel-

Butanoic acid, 3-hydroxy-2,2-dimethyl-, methyl ester, (3R)-

CAS:158169-13-2

Butanoic acid, 3-hydroxy-2,2-dimethyl-, methyl ester, (3R)-

2-Pentenoic acid, 3-phenyl-, methyl ester, (Z)-

CAS:157031-63-5

2-Pentenoic acid, 3-phenyl-, methyl ester, (Z)-

2-Pentenoic acid, 3-phenyl-, methyl ester, (E)-

CAS:153773-38-7

2-Pentenoic acid, 3-phenyl-, methyl ester, (E)-

Carbonic acid, cyclohexyl 2-propen-1-yl ester

CAS:14289-72-6

Carbonic acid, cyclohexyl 2-propen-1-yl ester

CAS:150943-32-1

Methyl 3-Hydroxy-4,4-dimethylpentanoate

3-Hydroxy-2,2-dimethyl-butyric Acid Ethyl Ester

CAS:69737-23-1

3-Hydroxy-2,2-dimethyl-butyric Acid Ethyl Ester

CAS:1517-70-0

(R)-1-(4-Methoxyphenyl)ethanol

CAS:1193-46-0

2,2-Dimethylcyclohexanol

Benzenepentanoic acid, b-methyl-, methyl ester

CAS:14983-20-1

Benzenepentanoic acid, b-methyl-, methyl ester

CAS:137333-66-5

1(3H)-Isobenzofuranone, 3-ethyl-, (R)-

Cyclopentanol, 2-(phenylmethoxy)-, (1R,2R)-rel-

CAS:135356-97-7

Cyclopentanol, 2-(phenylmethoxy)-, (1R,2R)-rel-

CAS:120540-25-2

1-Hexanol, 6-(methoxymethoxy)-

CAS:42070-92-8

(R)-1-(4-Methylphenyl)ethanol

CAS:2516-69-0

(R)-1-(2,4,6-Trimethylphenyl)ethanol

4-Morpholinecarboxylic acid, 2-propenyl ester

CAS:25070-77-3

4-Morpholinecarboxylic acid, 2-propenyl ester

Propanoic acid, 2,2-dimethyl-, 2-propenyl ester

CAS:15784-26-6

Propanoic acid, 2,2-dimethyl-, 2-propenyl ester

CAS:133766-24-2

Uridine, 2'-O-2-propenyl-

2-Hexenoic acid, 6-iodo-4,4-dimethyl-, ethyl ester, (E)-

CAS:139376-69-5

2-Hexenoic acid, 6-iodo-4,4-dimethyl-, ethyl ester, (E)-

Pentanamide, 3-hydroxy-N,N,4,4-tetramethyl-, (R)-

CAS:89209-15-4

Pentanamide, 3-hydroxy-N,N,4,4-tetramethyl-, (R)-

CAS:929-48-6

Octanoic acid, 8-oxo-

CAS:22616-89-3

5-PROP-1-EN-2-YLOXOLAN-2-ONE

Carbonic acid, 2-phenylethyl 2-propenyl ester

CAS:501014-38-6

Carbonic acid, 2-phenylethyl 2-propenyl ester

CAS:1517-71-1

(R)-1-(2,4,6-Trimethylphenyl)ethanol

CAS:37617-33-7

Cyclopentanol, 2,2-dimethyl-

Benzenepropanoic acid, b-hydroxy-, methyl ester, (bR)-

CAS:58692-70-9

Benzenepropanoic acid, b-hydroxy-, methyl ester, (bR)-

CAS:31108-34-6

(R)-1-(2,4,6-Trimethylphenyl)ethanol

2-Butenoic acid, 3-phenyl-, methyl ester, (E)-

CAS:3461-50-5

2-Butenoic acid, 3-phenyl-, methyl ester, (E)-

CAS:24892-50-0

2,4-Pentanediol, 3,3-dimethyl-

1-Naphthalenol, 1,2,3,4-tetrahydro-2,2-dimethyl-, (1R)-

CAS:24867-99-0

1-Naphthalenol, 1,2,3,4-tetrahydro-2,2-dimethyl-, (1R)-

CAS:51154-54-2

(1s)-1-(4-methylphenyl)ethanol

1-Naphthalenol, 1,2,3,4-tetrahydro-2,2-dimethyl-, (S)-

CAS:84275-49-0

1-Naphthalenol, 1,2,3,4-tetrahydro-2,2-dimethyl-, (S)-

CAS:5195-24-4

3-Pentanone,4,4-dimethyl-1-phenyl-

CAS:103532-78-1

Cyclohexanol, 2,2-dimethyl-, (1S)-

1-DIMETHOXYPHOSPHORYL-3,3-DIMETHYLBUTAN-2-ONE

CAS:7257-97-8

1-DIMETHOXYPHOSPHORYL-3,3-DIMETHYLBUTAN-2-ONE

1,2-Cyclopentanediol, monobenzoate, (1R,2R)-rel-

CAS:32651-77-7

1,2-Cyclopentanediol, monobenzoate, (1R,2R)-rel-

CAS:25966-65-8

3-Undecanol, 2,2-dimethyl-

Benzoicacid, 4,5-dichloro-2-[[(3aS,6R,7aR)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]-

CAS:193202-37-8

Benzoicacid, 4,5-dichloro-2-[[(3aS,6R,7aR)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]-

CAS:1572-97-0

(S)-1-(4-Methoxyphenyl)ethanol

CAS:6140-80-3

3-propan-2-yloxyprop-1-ene

Cyclohexanecarboxylicacid, 2-propen-1-yl ester

CAS:16491-63-7

Cyclohexanecarboxylicacid, 2-propen-1-yl ester

Benzenepropanoic acid,2-propen-1-yl ester

CAS:15814-45-6

Benzenepropanoic acid,2-propen-1-yl ester

1-Hexanol, 6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-

CAS:121671-77-0

1-Hexanol, 6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-

CAS:103532-77-0

Cyclopentanol, 2,2-dimethyl-, (S)-

1-Naphthalenol, 1,2,3,4-tetrahydro-2,2-dimethyl-

CAS:103041-51-6

1-Naphthalenol, 1,2,3,4-tetrahydro-2,2-dimethyl-

CAS:102536-89-0

2-Furanol, tetrahydro-3,3-dimethyl-

CAS:5390-04-5

4-Pentyn-1-ol

CAS:1823-90-1

2-Butanone,4-hydroxy-3,3-dimethyl-

CAS:53432-87-4

Ethyl cyclopropaneacetate

TRIS(ACETONITRILE)PENTAMETHYLCYCLOPENTADIENYLRUTHENIUM (I) HEXAFLUOROPHOSPHATE

CAS:99604-67-8

TRIS(ACETONITRILE)PENTAMETHYLCYCLOPENTADIENYLRUTHENIUM (I) HEXAFLUOROPHOSPHATE

(+)-3-BROMOCAMPHOR-10-SULFONIC ACID HYDRATE

CAS:76155-79-8

(+)-3-BROMOCAMPHOR-10-SULFONIC ACID HYDRATE

2,2-DIFLUORO-5H-[1,3]DIOXOLO[4,5-F]INDOLE-6,7-DIONE

CAS:74141-12-1

2,2-DIFLUORO-5H-[1,3]DIOXOLO[4,5-F]INDOLE-6,7-DIONE

N-{3-[(5-CHLORO-2-{[4-(4-METHYL-1-PIPERAZINYL)PHENYL]AMINO}-4-PYR<WBR />IMIDINYL)OXY]PHENYL}ACRYLAMIDE

CAS:74592-36-2

N-{3-[(5-CHLORO-2-{[4-(4-METHYL-1-PIPERAZINYL)PHENYL]AMINO}-4-PYRIMIDINYL)OXY]PHENYL}ACRYLAMIDE

CAS:71126-73-3

1-Hexanol, 6-(phenylmethoxy)-

(S)-1-(4-(Trifluoromethyl)phenyl)ethanol

CAS:99493-93-3

(S)-1-(4-(Trifluoromethyl)phenyl)ethanol

CAS:72656-47-4

7-FLUOROISOQUINOLINE

CAS:76-35-7

1,3-BUTANEDIOL,2,2-DIMETHYL-

(5-(Methoxycarbonyl)-2-methylphenyl)boronic acid

CAS:876189-18-3

(5-(Methoxycarbonyl)-2-methylphenyl)boronic acid

Benzoic acid, 2-(2-propenyl)-, methyl ester

CAS:61463-59-0

Benzoic acid, 2-(2-propenyl)-, methyl ester

CAS:60405-63-2

1,6-Hexanediol, monobenzoate

CAS:704910-24-7

2-BROMO-N-CYCLOPROPYL-4-NITROANILINE

CAS:75177-71-8

3,4,4-TRIMETHYLPENTANOIC ACID

CAS:1517-67-5

2-Butanol,3,3-dimethyl-, (2S)-

CAS:1572-96-9

2-Butanol,3,3-dimethyl-, (2R)-

CAS:1472-07-7

METHYL (R)-3-PHENYLBUTYRATE

CAS:1614-92-2

Piperidine,1-(1-cyclopenten-1-yl)-

CAS:434957-39-8

ETHYL 3-ACETAMIDO-3-PHENYLPROP-2-ENOATE

2-Butenoic acid, 3-phenyl-, methyl ester, (Z)-

CAS:26423-89-2

2-Butenoic acid, 3-phenyl-, methyl ester, (Z)-

CAS:26750-08-3

1-(Adamantan-1-yl)ethanol

CAS:30553-94-7

RUTHENIUM(2+);DIACETATE

CAS:3461-39-0

3-BROMO-1-PROPAN-D6-OL

Phosphonic acid,P-phenyl-, di-2-propen-1-yl ester

CAS:2948-89-2

Phosphonic acid,P-phenyl-, di-2-propen-1-yl ester

CAS:14289-65-7

Benzene,[2-(2-propen-1-yloxy)ethyl]-

CAS:109530-56-5

(1r)-2,2-dimethylcyclopentan-1-ol

2(3H)-Furanone,5-ethenyldihydro-5-methyl-

CAS:1073-11-6

2(3H)-Furanone,5-ethenyldihydro-5-methyl-

CAS:50902-74-4

METHYL 3,4,4-TRIMETHYLPENTANOATE

Butanoic acid, 3-(acetylamino)-, ethyl ester, (3S)-

CAS:247201-00-9

Butanoic acid, 3-(acetylamino)-, ethyl ester, (3S)-

CAS:439942-83-3

(2-METHYL-2-PROP-2-ENOXYPROPYL)BENZENE

CAS:41980-00-1

6-ETHENYLOXAN-2-ONE

CAS:130018-34-7

1-Pentyne, 5-(2-propenyloxy)-

CAS:43135-00-8

Et ester,N-Ac-(±)-3-Aminobutanoic acid

2-Propenoic acid, 3-(4-methoxyphenyl)-3-phenyl-, methyl ester, (2E)-

CAS:202391-21-7

2-Propenoic acid, 3-(4-methoxyphenyl)-3-phenyl-, methyl ester, (2E)-

CAS:108420-46-8

1-Pentene, 5-(2-propenyloxy)-

CAS:104752-25-2

2-prop-2-enoxy-2,3-dihydro-1h-indene

Ruthenium, [(1,2,5,6-h)-1,5-cyclooctadiene]bis[(1,2,3-h)-2-methyl-2-propenyl]- (9CI)

CAS:12289-94-0

Ruthenium, [(1,2,5,6-h)-1,5-cyclooctadiene]bis[(1,2,3-h)-2-methyl-2-propenyl]- (9CI)

CAS:609770-35-6

Pyridine, 2-(azidomethyl)-

CAS:298695-83-7

2-Butanone,1-(dimethylamino)-3,3-dimethyl-

CAS:56957-56-3

2-Butanone,1-(dimethylamino)-3,3-dimethyl-

CAS:23652-56-4

Ethyl cis-3-(acetamido)-2-butenoate

CAS:21963-38-2

2(3H)-Furanone,5-ethenyldihydro-