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The first conjugate addition reaction of terminal alkynes catalytic in copper:: Conjugate addition of alkynes in water
被引:141
作者
:
Knöpfel, TF
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Honggerberg, Lab Organ Chem, CH-8093 Zurich, Switzerland
ETH Honggerberg, Lab Organ Chem, CH-8093 Zurich, Switzerland
Knöpfel, TF
[
1
]
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Honggerberg, Lab Organ Chem, CH-8093 Zurich, Switzerland
ETH Honggerberg, Lab Organ Chem, CH-8093 Zurich, Switzerland
Carreira, EM
[
1
]
机构
:
[1]
ETH Honggerberg, Lab Organ Chem, CH-8093 Zurich, Switzerland
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2003年
/ 125卷
/ 20期
关键词
:
D O I
:
10.1021/ja035311z
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
We document that alkynyl copper reagents generated under aqueous conditions from terminal acetylenes, catalytic Cu(OAc)2, and sodium ascorbate undergo additions to Meldrum's acid-derived Michael acceptors at room temperature (Scheme 1). The additions are not only novel, but also constitute the first example of the conjugate addition reaction of an acetylide catalytic in copper. Copyright © 2003 American Chemical Society.
引用
收藏
页码:6054 / 6055
页数:2
相关论文
共 47 条
[1]
Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions
Alexakis, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Alexakis, A
Benhaim, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Benhaim, C
Rosse, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Rosse, S
Humam, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Humam, M
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(19)
: 5262
-
5263
[2]
A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes
Anand, NK
论文数:
0
引用数:
0
h-index:
0
机构:
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Anand, NK
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Carreira, EM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(39)
: 9687
-
9688
[3]
[Anonymous], MODERN ORGANOCOPPER
[4]
[Anonymous], 2000, CATALYTIC ASYMMETRIC
[5]
Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction
Aschwanden, P
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
Aschwanden, P
Frantz, DE
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
Frantz, DE
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
Carreira, EM
[J].
ORGANIC LETTERS,
2000,
2
(15)
: 2331
-
2333
[6]
IODOTRIMETHYLSILANE-PROMOTED ADDITIONS OF MONOORGANOCOPPER COMPOUNDS TO ALPHA,BETA-UNSATURATED KETONES, ESTERS, AND LACTONES
BERGDAHL, M
论文数:
0
引用数:
0
h-index:
0
机构:
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
BERGDAHL, M
ERIKSSON, M
论文数:
0
引用数:
0
h-index:
0
机构:
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
ERIKSSON, M
NILSSON, M
论文数:
0
引用数:
0
h-index:
0
机构:
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
NILSSON, M
OLSSON, T
论文数:
0
引用数:
0
h-index:
0
机构:
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
OLSSON, T
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1993,
58
(25)
: 7238
-
7244
[7]
Clean synthesis in water. Part 2: Uncatalysed condensation reaction of Meldrum's acid and aldehydes
Bigi, F
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Bigi, F
Carloni, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Carloni, S
论文数:
引用数:
h-index:
机构:
Ferrari, L
论文数:
引用数:
h-index:
机构:
Maggi, R
Mazzacani, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Mazzacani, A
Sartori, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Sartori, G
[J].
TETRAHEDRON LETTERS,
2001,
42
(31)
: 5203
-
5205
[8]
Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions
Boyall, D
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
Boyall, D
Frantz, DE
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
Frantz, DE
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
Carreira, EM
[J].
ORGANIC LETTERS,
2002,
4
(15)
: 2605
-
2606
[9]
Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes
Boyall, D
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Boyall, D
López, F
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
López, F
Sasaki, H
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Sasaki, H
Frantz, D
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Frantz, D
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Carreira, EM
[J].
ORGANIC LETTERS,
2000,
2
(26)
: 4233
-
4236
[10]
BRUHN M, 1976, TETRAHEDRON LETT, V17, P235
←
1
2
3
4
5
→
共 47 条
[1]
Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions
Alexakis, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Alexakis, A
Benhaim, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Benhaim, C
Rosse, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Rosse, S
Humam, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland
Humam, M
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(19)
: 5262
-
5263
[2]
A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes
Anand, NK
论文数:
0
引用数:
0
h-index:
0
机构:
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Anand, NK
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Carreira, EM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(39)
: 9687
-
9688
[3]
[Anonymous], MODERN ORGANOCOPPER
[4]
[Anonymous], 2000, CATALYTIC ASYMMETRIC
[5]
Synthesis of 2,3-dihydroisoxazoles from propargylic N-hydroxylamines via Zn(II)-catalyzed ring-closure reaction
Aschwanden, P
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
Aschwanden, P
Frantz, DE
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
Frantz, DE
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland
Carreira, EM
[J].
ORGANIC LETTERS,
2000,
2
(15)
: 2331
-
2333
[6]
IODOTRIMETHYLSILANE-PROMOTED ADDITIONS OF MONOORGANOCOPPER COMPOUNDS TO ALPHA,BETA-UNSATURATED KETONES, ESTERS, AND LACTONES
BERGDAHL, M
论文数:
0
引用数:
0
h-index:
0
机构:
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
BERGDAHL, M
ERIKSSON, M
论文数:
0
引用数:
0
h-index:
0
机构:
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
ERIKSSON, M
NILSSON, M
论文数:
0
引用数:
0
h-index:
0
机构:
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
NILSSON, M
OLSSON, T
论文数:
0
引用数:
0
h-index:
0
机构:
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
CHALMERS UNIV TECHNOL,DEPT ORGAN CHEM,S-41296 GOTHENBURG,SWEDEN
OLSSON, T
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1993,
58
(25)
: 7238
-
7244
[7]
Clean synthesis in water. Part 2: Uncatalysed condensation reaction of Meldrum's acid and aldehydes
Bigi, F
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Bigi, F
Carloni, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Carloni, S
论文数:
引用数:
h-index:
机构:
Ferrari, L
论文数:
引用数:
h-index:
机构:
Maggi, R
Mazzacani, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Mazzacani, A
Sartori, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Univ Parma, Dipartimemto Chim Organ & Ind, I-43100 Parma, Italy
Sartori, G
[J].
TETRAHEDRON LETTERS,
2001,
42
(31)
: 5203
-
5205
[8]
Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions
Boyall, D
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
Boyall, D
Frantz, DE
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
Frantz, DE
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
Carreira, EM
[J].
ORGANIC LETTERS,
2002,
4
(15)
: 2605
-
2606
[9]
Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes
Boyall, D
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Boyall, D
López, F
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
López, F
Sasaki, H
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Sasaki, H
Frantz, D
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Frantz, D
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Carreira, EM
[J].
ORGANIC LETTERS,
2000,
2
(26)
: 4233
-
4236
[10]
BRUHN M, 1976, TETRAHEDRON LETT, V17, P235
←
1
2
3
4
5
→