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Enantioselective hydrogenation of aromatic ketones catalyzed by Ru complexes of Goodwin-Lions-type sp2N/sp3N hybrid Ligands R-BINAN-R′-Py
被引:104
作者
:
Huang, Hanmin
论文数:
0
引用数:
0
h-index:
0
机构:
Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
Huang, Hanmin
Okuno, Tomoko
论文数:
0
引用数:
0
h-index:
0
机构:
Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
Okuno, Tomoko
Tsuda, Kazuomi
论文数:
0
引用数:
0
h-index:
0
机构:
Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
Tsuda, Kazuomi
Yoshimura, Masahiro
论文数:
0
引用数:
0
h-index:
0
机构:
Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
Yoshimura, Masahiro
Kitamura, Masato
论文数:
0
引用数:
0
h-index:
0
机构:
Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
Kitamura, Masato
[
1
]
机构
:
[1]
Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2]
Nagoya Univ, Dept Chem, Chikusa Ku, Nagoya, Aichi 4648602, Japan
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2006年
/ 128卷
/ 27期
关键词
:
D O I
:
10.1021/ja062451a
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R′-Py possessing a C2 axis binaphthyl skeleton have been designed and synthesized. Combination of the new non-phosphine ligand with Ru(π-CH2C(CH3)CH2)2(cod) has been revealed to catalyze the hydrogenation of aromatic ketones with high enantioselectivity of up to 99% ee. The reaction proceeds essentially without the need for any bases, but the reactivity is enhanced by the addition of KOt-C4H9 attaining an S/C ratio of up to 10000. The success should expand the range of possibilities in designing catalysts not only for hydrogenation but also for many other reactions. Copyright © 2006 American Chemical Society.
引用
收藏
页码:8716 / 8717
页数:2
相关论文
共 32 条
[1]
KINETICS AND MECHANISM OF CATALYSIS OF THE ASYMMETRIC HYDROGENATION OF ALPHA-BETA-UNSATURATED CARBOXYLIC-ACIDS BY BIS(CARBOXYLATO)(2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL)-RUTHENIUM(II), [RUII(BINAP)(O2CR)2]
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ASHBY, MT
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0
引用数:
0
h-index:
0
机构:
UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637
UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637
ASHBY, MT
;
HALPERN, J
论文数:
0
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0
h-index:
0
机构:
UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637
UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637
HALPERN, J
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1991,
113
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:589
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Breuzard JAJ, 2005, TOP ORGANOMETAL CHEM, V15, P231
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EXHAUSTIVE EXAMINATION OF CHIRAL CONFIGURATIONS OF EDGES ON A REGULAR OCTAHEDRON - ANALYSIS OF THE POSSIBILITIES OF ASSIGNING CHIRALITY DESCRIPTORS WITHIN A GENERALIZED DELTA-LAMBDA-SYSTEM
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0
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0
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UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
BRORSON, M
;
DAMHUS, T
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0
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0
h-index:
0
机构:
UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
DAMHUS, T
;
SCHAFFER, CE
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0
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UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
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Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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GENET, JP
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0
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0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
GENET, JP
;
PINEL, C
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
PINEL, C
;
RATOVELOMANANAVIDAL, V
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
RATOVELOMANANAVIDAL, V
;
MALLART, S
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
MALLART, S
;
PFISTER, X
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
PFISTER, X
;
DEANDRADE, MCC
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
DEANDRADE, MCC
;
LAFFITTE, JA
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0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
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0
h-index:
0
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Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Hamilton, RJ
;
Leong, CG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Leong, CG
;
Bigam, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Bigam, G
;
Miskolzie, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Miskolzie, M
;
Bergens, SH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Bergens, SH
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
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:4152
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Mechanistic insights into the phosphine-free RuCp☆-diamine-catalyzed hydrogenation of aryl ketones:: Experimental and theoretical evidence for an alcohol-mediated dihydrogen activation
[J].
Hedberg, C
论文数:
0
引用数:
0
h-index:
0
机构:
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Hedberg, C
;
Källström, K
论文数:
0
引用数:
0
h-index:
0
机构:
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Källström, K
;
Arvidsson, PI
论文数:
0
引用数:
0
h-index:
0
机构:
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Arvidsson, PI
;
Brandt, P
论文数:
0
引用数:
0
h-index:
0
机构:
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Brandt, P
;
Andersson, PG
论文数:
0
引用数:
0
h-index:
0
机构:
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Andersson, PG
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
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:15083
-15090
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Bifunctional transition metal-based molecular catalysts for asymmetric syntheses
[J].
Ikariya, T
论文数:
0
引用数:
0
h-index:
0
机构:
Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan
Ikariya, T
;
论文数:
引用数:
h-index:
机构:
Murata, K
;
Noyori, R
论文数:
0
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Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan
Noyori, R
.
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2006,
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←
1
2
3
4
→
共 32 条
[1]
KINETICS AND MECHANISM OF CATALYSIS OF THE ASYMMETRIC HYDROGENATION OF ALPHA-BETA-UNSATURATED CARBOXYLIC-ACIDS BY BIS(CARBOXYLATO)(2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL)-RUTHENIUM(II), [RUII(BINAP)(O2CR)2]
[J].
ASHBY, MT
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637
UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637
ASHBY, MT
;
HALPERN, J
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637
UNIV CHICAGO,DEPT CHEM,CHICAGO,IL 60637
HALPERN, J
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1991,
113
(02)
:589
-594
[2]
Breuzard JAJ, 2005, TOP ORGANOMETAL CHEM, V15, P231
[3]
EXHAUSTIVE EXAMINATION OF CHIRAL CONFIGURATIONS OF EDGES ON A REGULAR OCTAHEDRON - ANALYSIS OF THE POSSIBILITIES OF ASSIGNING CHIRALITY DESCRIPTORS WITHIN A GENERALIZED DELTA-LAMBDA-SYSTEM
[J].
BRORSON, M
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
BRORSON, M
;
DAMHUS, T
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
DAMHUS, T
;
SCHAFFER, CE
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
UNIV COPENHAGEN,HC ORSTED INST,DEPT CHEM 1,DK-2100 COPENHAGEN O,DENMARK
SCHAFFER, CE
.
INORGANIC CHEMISTRY,
1983,
22
(11)
:1569
-1573
[4]
Evidence for the participation of a high-valent iron-oxo species in stereospecific alkane hydroxylation by a non-heme iron catalyst
[J].
Chen, K
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
Chen, K
;
Que, L
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
Que, L
.
CHEMICAL COMMUNICATIONS,
1999,
(15)
:1375
-1376
[5]
KINETICS AND THERMODYNAMICS OF KETO-ENOL-TAUTOMERISM OF SIMPLE CARBONYL-COMPOUNDS - AN APPROACH BASED ON A KINETIC-STUDY OF HALOGENATION AT LOW HALOGEN CONCENTRATIONS
[J].
DUBOIS, JE
论文数:
0
引用数:
0
h-index:
0
DUBOIS, JE
;
ELALAOUI, M
论文数:
0
引用数:
0
h-index:
0
ELALAOUI, M
;
TOULLEC, J
论文数:
0
引用数:
0
h-index:
0
TOULLEC, J
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1981,
103
(18)
:5393
-5401
[6]
NOVEL, GENERAL-SYNTHESIS OF THE CHIRAL CATALYSTS DIPHOSPHINE-RUTHENIUM(II) DIALLYL COMPLEXES AND A NEW PRACTICAL IN-SITU PREPARATION OF CHIRAL RUTHENIUM(II) CATALYSTS
[J].
GENET, JP
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
GENET, JP
;
PINEL, C
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
PINEL, C
;
RATOVELOMANANAVIDAL, V
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
RATOVELOMANANAVIDAL, V
;
MALLART, S
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
MALLART, S
;
PFISTER, X
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
PFISTER, X
;
DEANDRADE, MCC
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
DEANDRADE, MCC
;
LAFFITTE, JA
论文数:
0
引用数:
0
h-index:
0
机构:
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
ELF AQUITAINE,GRL,DEPT CHIM FINE & BIOCONVERS,F-64170 LACQ,FRANCE
LAFFITTE, JA
.
TETRAHEDRON-ASYMMETRY,
1994,
5
(04)
:665
-674
[7]
QUADRIDENTATE CHELATE COMPOUNDS .2.
[J].
GOODWIN, HA
论文数:
0
引用数:
0
h-index:
0
GOODWIN, HA
;
LIONS, F
论文数:
0
引用数:
0
h-index:
0
LIONS, F
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1960,
82
(19)
:5013
-5023
[8]
A ruthenium-dihydrogen putative intermediate in ketone hydrogenation
[J].
Hamilton, RJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Hamilton, RJ
;
Leong, CG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Leong, CG
;
Bigam, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Bigam, G
;
Miskolzie, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Miskolzie, M
;
Bergens, SH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
Bergens, SH
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(12)
:4152
-4153
[9]
Mechanistic insights into the phosphine-free RuCp☆-diamine-catalyzed hydrogenation of aryl ketones:: Experimental and theoretical evidence for an alcohol-mediated dihydrogen activation
[J].
Hedberg, C
论文数:
0
引用数:
0
h-index:
0
机构:
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Hedberg, C
;
Källström, K
论文数:
0
引用数:
0
h-index:
0
机构:
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Källström, K
;
Arvidsson, PI
论文数:
0
引用数:
0
h-index:
0
机构:
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Arvidsson, PI
;
Brandt, P
论文数:
0
引用数:
0
h-index:
0
机构:
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Brandt, P
;
Andersson, PG
论文数:
0
引用数:
0
h-index:
0
机构:
Uppsala Univ, Dept Chem, S-75124 Uppsala, Sweden
Andersson, PG
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(43)
:15083
-15090
[10]
Bifunctional transition metal-based molecular catalysts for asymmetric syntheses
[J].
Ikariya, T
论文数:
0
引用数:
0
h-index:
0
机构:
Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan
Ikariya, T
;
论文数:
引用数:
h-index:
机构:
Murata, K
;
Noyori, R
论文数:
0
引用数:
0
h-index:
0
机构:
Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan
Noyori, R
.
ORGANIC & BIOMOLECULAR CHEMISTRY,
2006,
4
(03)
:393
-406
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