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Enantioselective Alkynylbenzaldehyde Cyclizations Catalyzed by Chiral Gold(I) Acyclic Diaminocarbene Complexes Containing Weak Au-Arene Interactions
被引:196
作者
:
Handa, Sachin
论文数:
0
引用数:
0
h-index:
0
机构:
Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
Handa, Sachin
[
1
]
Slaughter, LeGrande M.
论文数:
0
引用数:
0
h-index:
0
机构:
Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
Slaughter, LeGrande M.
[
1
]
机构
:
[1]
Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2012年
/ 51卷
/ 12期
基金
:
美国国家科学基金会;
关键词
:
asymmetric catalysis;
carbene ligands;
domino reactions;
gold;
metal-p interactions;
ASYMMETRIC ALDOL REACTION;
CROSS-COUPLING REACTIONS;
CYCLIC ALKENYL ETHERS;
HETEROCYCLIC CARBENES;
PI-INTERACTIONS;
SOLID-STATE;
LEWIS-ACID;
LIGANDS;
PALLADIUM;
ALDEHYDES;
D O I
:
10.1002/anie.201107789
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
Hold me close: Highly enantioselective catalysis of tandem acetalization/cycloisomerization reactions of o-alkynylbenzaldehydes has been achieved using gold complexes of chiral acyclic diaminocarbene ligands that have electron-deficient aryl substituents. X-ray crystallography and DFT calculations implicate weak gold-arene interactions - absent in the case of simple phenyl substituents - that define the chirality of the substrate binding site. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2912 / 2915
页数:4
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Acyclic diaminocarbenes: simple, versatile ligands for cross-coupling reactions
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Silver versus gold catalysis in tandem reactions of carbonyl functions onto alkynes: A versatile access to furoquinoline and pyranoquinoline cores
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Ligand effects in homogeneous Au catalysis
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Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
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Gold-catalyzed organic reactions
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Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
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From Isonitriles to Carbenes: Synthesis of New NAC- and NHC-Palladium(II) Compounds and Their Catalytic Activity
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Heidelberg Univ, Inst Organ Chem, D-69221 Heidelberg, Germany
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Lothschuetz, Christian
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Heidelberg Univ, Inst Organ Chem, D-69221 Heidelberg, Germany
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Lothschuetz, Christian
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Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
Lothschuetz, Christian
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Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
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[30]
Herrero-Gomez E., 2006, Angewandte Chemie, V118, P5581
←
1
2
3
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5
6
7
8
→
共 72 条
[21]
Acyclic diaminocarbenes: simple, versatile ligands for cross-coupling reactions
Dhudshia, B
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada
Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada
Dhudshia, B
Thadani, AN
论文数:
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引用数:
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h-index:
0
机构:
Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada
Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada
Thadani, AN
[J].
CHEMICAL COMMUNICATIONS,
2006,
(06)
: 668
-
670
[22]
Metal-mediated asymmetric alkylation using chiral N-heterocyclic carbenes derived from chiral amines
Douthwaite, Richard E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ York, Dept Chem, York YO24 4ED, N Yorkshire, England
Univ York, Dept Chem, York YO24 4ED, N Yorkshire, England
Douthwaite, Richard E.
[J].
COORDINATION CHEMISTRY REVIEWS,
2007,
251
(5-6)
: 702
-
717
[23]
Furstner A., 2007, Angew. Chem, V119, P3478, DOI DOI 10.1002/ANGE.200604335
[24]
Gade LH, 2007, TOP ORGANOMETAL CHEM, V21, P117, DOI 10.1007/3418_028
[25]
Silver versus gold catalysis in tandem reactions of carbonyl functions onto alkynes: A versatile access to furoquinoline and pyranoquinoline cores
Godet, Thomas
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Lyon 1, CNRS, ICBMS, UMR 5246, F-69622 Villeurbanne, France
Godet, Thomas
Vaxelaire, Carine
论文数:
0
引用数:
0
h-index:
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机构:
Univ Lyon 1, CNRS, ICBMS, UMR 5246, F-69622 Villeurbanne, France
Vaxelaire, Carine
Michel, Carine
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引用数:
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h-index:
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Univ Lyon 1, CNRS, ICBMS, UMR 5246, F-69622 Villeurbanne, France
Michel, Carine
Milet, Anne
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Lyon 1, CNRS, ICBMS, UMR 5246, F-69622 Villeurbanne, France
Milet, Anne
论文数:
引用数:
h-index:
机构:
Belmont, Philippe
[J].
CHEMISTRY-A EUROPEAN JOURNAL,
2007,
13
(19)
: 5632
-
5641
[26]
Ligand effects in homogeneous Au catalysis
Gorin, David J.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Gorin, David J.
Sherry, Benjamin D.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Sherry, Benjamin D.
Toste, F. Dean
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Toste, F. Dean
[J].
CHEMICAL REVIEWS,
2008,
108
(08)
: 3351
-
3378
[27]
Gold-catalyzed organic reactions
Hashmi, A. Stephen K.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
Hashmi, A. Stephen K.
[J].
CHEMICAL REVIEWS,
2007,
107
(07)
: 3180
-
3211
[28]
From Isonitriles to Carbenes: Synthesis of New NAC- and NHC-Palladium(II) Compounds and Their Catalytic Activity
Hashmi, A. Stephen K.
论文数:
0
引用数:
0
h-index:
0
机构:
Heidelberg Univ, Inst Organ Chem, D-69221 Heidelberg, Germany
Heidelberg Univ, Inst Organ Chem, D-69221 Heidelberg, Germany
Hashmi, A. Stephen K.
Lothschuetz, Christian
论文数:
0
引用数:
0
h-index:
0
机构:
Heidelberg Univ, Inst Organ Chem, D-69221 Heidelberg, Germany
Heidelberg Univ, Inst Organ Chem, D-69221 Heidelberg, Germany
Lothschuetz, Christian
Boehling, Constantin
论文数:
0
引用数:
0
h-index:
0
机构:
Heidelberg Univ, Inst Organ Chem, D-69221 Heidelberg, Germany
Heidelberg Univ, Inst Organ Chem, D-69221 Heidelberg, Germany
Boehling, Constantin
Rominger, Frank
论文数:
0
引用数:
0
h-index:
0
机构:
Heidelberg Univ, Inst Organ Chem, D-69221 Heidelberg, Germany
Heidelberg Univ, Inst Organ Chem, D-69221 Heidelberg, Germany
Rominger, Frank
[J].
ORGANOMETALLICS,
2011,
30
(08)
: 2411
-
2417
[29]
New and Easily Accessible Nitrogen Acyclic Gold(I) Carbenes: Structure and Application in the Gold-Catalyzed Phenol Synthesis as well as the Hydration of Alkynes
Hashmi, A. Stephen K.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
Hashmi, A. Stephen K.
Hengst, Tobias
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
Hengst, Tobias
Lothschuetz, Christian
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
Lothschuetz, Christian
Rominger, Frank
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
Rominger, Frank
[J].
ADVANCED SYNTHESIS & CATALYSIS,
2010,
352
(08)
: 1315
-
1337
[30]
Herrero-Gomez E., 2006, Angewandte Chemie, V118, P5581
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1
2
3
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5
6
7
8
→