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Regioselective synthesis of γ-amino esters, nitriles, sulfones, and pyrrolidinones by nickel-catalyzed reductive coupling of aldimines and activated alkenes
被引:51
作者
:
Yeh, Chien-Hung
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
Yeh, Chien-Hung
[
1
]
Korivi, Rajendra Prasad
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
Korivi, Rajendra Prasad
[
1
]
论文数:
引用数:
h-index:
机构:
Cheng, Chien-Hong
[
1
]
机构
:
[1]
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2008年
/ 47卷
/ 26期
关键词
:
cross-coupling;
homogeneous catalysis;
N ligands;
nickel;
pyrrolidinones;
D O I
:
10.1002/anie.200800825
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) A couple of alternatives: An efficient method has been developed for the synthesis of γ-amino derivatives and pyrrolidinones from readily available starting materials by using a nickel-phenanthroline complex (see scheme). The reaction proceeds by the formation of a C-C bond at the β-carbon atom, instead of the more usual α-carbon atom, of a conjugated alkene via an azanickelacycle intermediate. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4892 / 4895
页数:4
相关论文
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[1]
Structure of an η1 nickel O-enolate:: Mechanistic implications in catalytic enyne cyclizations
[J].
Amarasinghe, KKD
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0
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Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
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Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
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Cobalt-catalyzed reductive coupling of activated alkenes with alkynes
[J].
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Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
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Cheng, Chien-Hong
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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129
(39)
:12032
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[4]
Cobalt-catalyzed diastereoselective reductive [3+2] cycloaddition of allenes and enones
[J].
Chang, Hong-Tai
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Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
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Cobalt-catalyzed intramolecular [2+2+2] cocyclotrimerization of nitrilediynes: An efficient route to tetra- and pentacyclic pyridine derivatives
[J].
Chang, Hong-Tai
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Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile:: A facile route to indenols and indenes
[J].
Chang, KJ
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0
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[7]
Diverse reactivity manifolds of alkynyl enone- and alkynyl enal-derived nickelacycles: Discovery of nickel-promoted [3+2] and [2+1] cycloadditions
[J].
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Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
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;
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0
h-index:
0
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Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
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;
Heeg, MJ
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0
引用数:
0
h-index:
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Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
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Montgomery, J
.
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[J].
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;
LARGIS, EE
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论文数:
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引用数:
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.
JOURNAL OF MEDICINAL CHEMISTRY,
1983,
26
(10)
:1411
-1421
←
1
2
3
4
5
6
7
→
共 67 条
[1]
Structure of an η1 nickel O-enolate:: Mechanistic implications in catalytic enyne cyclizations
[J].
Amarasinghe, KKD
论文数:
0
引用数:
0
h-index:
0
机构:
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Amarasinghe, KKD
;
Chowdhury, SK
论文数:
0
引用数:
0
h-index:
0
机构:
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Chowdhury, SK
;
Heeg, MJ
论文数:
0
引用数:
0
h-index:
0
机构:
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Heeg, MJ
;
论文数:
引用数:
h-index:
机构:
Montgomery, J
.
ORGANOMETALLICS,
2001,
20
(03)
:370
-372
[2]
Ester-based precursors to increase the bioavailability of quercetin
[J].
Biasutto, Lucia
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Padua, Dept Biomed Sci, I-35100 Padua, Italy
Biasutto, Lucia
;
Marotta, Ester
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Padua, Dept Biomed Sci, I-35100 Padua, Italy
Marotta, Ester
;
De Marchi, Umberto
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Padua, Dept Biomed Sci, I-35100 Padua, Italy
De Marchi, Umberto
;
论文数:
引用数:
h-index:
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Zoratti, Mario
;
论文数:
引用数:
h-index:
机构:
Paradisi, Cristina
.
JOURNAL OF MEDICINAL CHEMISTRY,
2007,
50
(02)
:241
-253
[3]
Cobalt-catalyzed reductive coupling of activated alkenes with alkynes
[J].
Chang, Hong-Tai
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
Chang, Hong-Tai
;
论文数:
引用数:
h-index:
机构:
Jayanth, Thiruvellore Thatai
;
Wang, Chun-Chih
论文数:
0
引用数:
0
h-index:
0
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Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
Wang, Chun-Chih
;
论文数:
引用数:
h-index:
机构:
Cheng, Chien-Hong
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007,
129
(39)
:12032
-12041
[4]
Cobalt-catalyzed diastereoselective reductive [3+2] cycloaddition of allenes and enones
[J].
Chang, Hong-Tai
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30043, Taiwan
Chang, Hong-Tai
;
论文数:
引用数:
h-index:
机构:
Jayanth, Thiruvellore Thatai
;
论文数:
引用数:
h-index:
机构:
Cheng, Chien-Hong
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007,
129
(14)
:4166
-+
[5]
Cobalt-catalyzed intramolecular [2+2+2] cocyclotrimerization of nitrilediynes: An efficient route to tetra- and pentacyclic pyridine derivatives
[J].
Chang, Hong-Tai
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
Chang, Hong-Tai
;
论文数:
引用数:
h-index:
机构:
Jeganmohan, Masilamani
;
论文数:
引用数:
h-index:
机构:
Cheng, Chien-Hong
.
ORGANIC LETTERS,
2007,
9
(03)
:505
-508
[6]
Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile:: A facile route to indenols and indenes
[J].
Chang, KJ
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
Chang, KJ
;
Rayabarapu, DK
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
Rayabarapu, DK
;
Cheng, CH
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
Cheng, CH
.
JOURNAL OF ORGANIC CHEMISTRY,
2004,
69
(14)
:4781
-4787
[7]
Diverse reactivity manifolds of alkynyl enone- and alkynyl enal-derived nickelacycles: Discovery of nickel-promoted [3+2] and [2+1] cycloadditions
[J].
Chowdhury, SK
论文数:
0
引用数:
0
h-index:
0
机构:
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Chowdhury, SK
;
Amarasinghe, KKD
论文数:
0
引用数:
0
h-index:
0
机构:
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Amarasinghe, KKD
;
Heeg, MJ
论文数:
0
引用数:
0
h-index:
0
机构:
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
Heeg, MJ
;
论文数:
引用数:
h-index:
机构:
Montgomery, J
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(28)
:6775
-6776
[8]
DENHEZ C, 2006, ARKIVOC, V6, P161
[9]
Asymmetric synthesis of di- and trisubstituted pyrrolidinones via zirconium-mediated intramolecular coupling of N-3-alkenyl carbamates
[J].
Denhez, Clement
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, UMR 6519, React Select & Applicat, F-51687 Reims 2, France
Denhez, Clement
;
Vasse, Jean-Luc
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, UMR 6519, React Select & Applicat, F-51687 Reims 2, France
Vasse, Jean-Luc
;
Harakat, Dominique
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, UMR 6519, React Select & Applicat, F-51687 Reims 2, France
Harakat, Dominique
;
Szymoniak, Jan
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, UMR 6519, React Select & Applicat, F-51687 Reims 2, France
CNRS, UMR 6519, React Select & Applicat, F-51687 Reims 2, France
Szymoniak, Jan
.
TETRAHEDRON-ASYMMETRY,
2007,
18
(03)
:424
-434
[10]
POTENTIAL ANTI-ATHEROSCLEROTIC AGENTS .4. [(FUNCTIONALIZED-ALKYL)AMINO]BENZOIC ACID ANALOGS OF CETABEN
[J].
DEVRIES, VG
论文数:
0
引用数:
0
h-index:
0
DEVRIES, VG
;
LARGIS, EE
论文数:
0
引用数:
0
h-index:
0
LARGIS, EE
;
MINER, TG
论文数:
0
引用数:
0
h-index:
0
MINER, TG
;
SHEPHERD, RG
论文数:
0
引用数:
0
h-index:
0
SHEPHERD, RG
;
UPESLACIS, J
论文数:
0
引用数:
0
h-index:
0
UPESLACIS, J
.
JOURNAL OF MEDICINAL CHEMISTRY,
1983,
26
(10)
:1411
-1421
←
1
2
3
4
5
6
7
→