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Enantioselective indole Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes
被引:233
作者
:
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
[
1
]
Scheidt, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Scheidt, KA
[
1
]
Fandrick, KR
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Fandrick, KR
[
1
]
Lam, HW
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Lam, HW
[
1
]
Wu, J
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Wu, J
[
1
]
机构
:
[1]
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2003年
/ 125卷
/ 36期
关键词
:
D O I
:
10.1021/ja036985c
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
A highly enantioselective Friedel-Crafts alkylation of electron-rich aromatic nucleophiles catalyzed by scandium(III) triflate-pyridyl(bis)oxazoline complexes has been accomplished. The reaction involves α,β-unsaturated acyl phosphonates as electrophiles and primarily substituted indoles as nucleophiles. The reactive acyl phosphonate product is converted to the corresponding ester or amide in good overall yield by adding an alcohol or amine directly to the reaction mixture. Copyright © 2003 American Chemical Society.
引用
收藏
页码:10780 / 10781
页数:2
相关论文
共 19 条
[1]
Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis
Austin, JF
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0
引用数:
0
h-index:
0
机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
Austin, JF
MacMillan, DWC
论文数:
0
引用数:
0
h-index:
0
机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
MacMillan, DWC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
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1173
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Concise synthesis of conformationally constrained pybox ligands
Davies, IW
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0
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0
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0
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Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065
Davies, IW
Gerena, L
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065
Gerena, L
Lu, N
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065
Lu, N
Larsen, RD
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065
Larsen, RD
Reider, PJ
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0
引用数:
0
h-index:
0
机构:
Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065
Reider, PJ
[J].
JOURNAL OF ORGANIC CHEMISTRY,
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Synthesis of N-protected α-amino aldehydes from their morpholine amide derivatives
Douat, C
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0
引用数:
0
h-index:
0
机构:
Univ Montpellier 1, CNRS, LAPP, F-34060 Montpellier, France
Douat, C
Heitz, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montpellier 1, CNRS, LAPP, F-34060 Montpellier, France
Heitz, A
Martinez, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montpellier 1, CNRS, LAPP, F-34060 Montpellier, France
Martinez, J
Fehrentz, JA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montpellier 1, CNRS, LAPP, F-34060 Montpellier, France
Fehrentz, JA
[J].
TETRAHEDRON LETTERS,
2000,
41
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40
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A general method for the enantioselective synthesis of pantolactone derivatives
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Wu, J
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Wu, J
Masse, CE
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Masse, CE
MacMillan, DWC
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
MacMillan, DWC
[J].
ORGANIC LETTERS,
2002,
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3382
[5]
C2-symmetric Sc(III)-complexes chiral Lewis acids.: Catalytic enantioselective aldol additions glyoxylate esters
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Masse, CE
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Masse, CE
Wu, J
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Wu, J
[J].
ORGANIC LETTERS,
2002,
4
(20)
: 3375
-
3378
[6]
Highly enantioselective syntheses of homopropargylic alcohols and dihydrofurans catalyzed by a bis(oxazolinyl)pyridine-scandium triflate complex
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Sweeney, ZK
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Sweeney, ZK
Rovis, T
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Rovis, T
Tedrow, JS
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Tedrow, JS
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(48)
: 12095
-
12096
[7]
Enantioselective synthesis of dihydropyrans. Catalysis of hetero Diels-Alder reactions by bis(oxazoline) copper(II) complexes
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
Johnson, JS
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Johnson, JS
Olhava, EJ
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Olhava, EJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(08)
: 1635
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1649
[8]
Jensen KB, 2001, ANGEW CHEM INT EDIT, V40, P160, DOI 10.1002/1521-3773(20010105)40:1<160::AID-ANIE160>3.0.CO
[9]
2-S
[10]
A CHIRAL SCANDIUM CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER REACTIONS
KOBAYASHI, S
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku
KOBAYASHI, S
ARAKI, M
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku
ARAKI, M
HACHIYA, I
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku
HACHIYA, I
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1994,
59
(14)
: 3758
-
3759
←
1
2
→
共 19 条
[1]
Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis
Austin, JF
论文数:
0
引用数:
0
h-index:
0
机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
Austin, JF
MacMillan, DWC
论文数:
0
引用数:
0
h-index:
0
机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
MacMillan, DWC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(07)
: 1172
-
1173
[2]
Concise synthesis of conformationally constrained pybox ligands
Davies, IW
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065
Davies, IW
Gerena, L
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065
Gerena, L
Lu, N
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065
Lu, N
Larsen, RD
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065
Larsen, RD
Reider, PJ
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Process Research, Merck and Co., Inc., Rahway, NJ 07065
Reider, PJ
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1996,
61
(26)
: 9629
-
9630
[3]
Synthesis of N-protected α-amino aldehydes from their morpholine amide derivatives
Douat, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montpellier 1, CNRS, LAPP, F-34060 Montpellier, France
Douat, C
Heitz, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montpellier 1, CNRS, LAPP, F-34060 Montpellier, France
Heitz, A
Martinez, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montpellier 1, CNRS, LAPP, F-34060 Montpellier, France
Martinez, J
Fehrentz, JA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montpellier 1, CNRS, LAPP, F-34060 Montpellier, France
Fehrentz, JA
[J].
TETRAHEDRON LETTERS,
2000,
41
(01)
: 37
-
40
[4]
A general method for the enantioselective synthesis of pantolactone derivatives
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Wu, J
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Wu, J
Masse, CE
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Masse, CE
MacMillan, DWC
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
MacMillan, DWC
[J].
ORGANIC LETTERS,
2002,
4
(20)
: 3379
-
3382
[5]
C2-symmetric Sc(III)-complexes chiral Lewis acids.: Catalytic enantioselective aldol additions glyoxylate esters
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Masse, CE
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Masse, CE
Wu, J
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Wu, J
[J].
ORGANIC LETTERS,
2002,
4
(20)
: 3375
-
3378
[6]
Highly enantioselective syntheses of homopropargylic alcohols and dihydrofurans catalyzed by a bis(oxazolinyl)pyridine-scandium triflate complex
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Sweeney, ZK
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Sweeney, ZK
Rovis, T
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Rovis, T
Tedrow, JS
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Tedrow, JS
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(48)
: 12095
-
12096
[7]
Enantioselective synthesis of dihydropyrans. Catalysis of hetero Diels-Alder reactions by bis(oxazoline) copper(II) complexes
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
Johnson, JS
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Johnson, JS
Olhava, EJ
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Olhava, EJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(08)
: 1635
-
1649
[8]
Jensen KB, 2001, ANGEW CHEM INT EDIT, V40, P160, DOI 10.1002/1521-3773(20010105)40:1<160::AID-ANIE160>3.0.CO
[9]
2-S
[10]
A CHIRAL SCANDIUM CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER REACTIONS
KOBAYASHI, S
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku
KOBAYASHI, S
ARAKI, M
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku
ARAKI, M
HACHIYA, I
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Tokyo 162, Kagurazaka, Shinjuku-ku
HACHIYA, I
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1994,
59
(14)
: 3758
-
3759
←
1
2
→