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Enantioselective addition of amines to ketenes catalyzed by a planar-chiral derivative of PPY: Possible intervention of chiral Bronsted-acid catalysis
被引:116
作者
:
Hodous, BL
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Hodous, BL
[
1
]
Fu, GC
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Fu, GC
[
1
]
机构
:
[1]
MIT, Dept Chem, Cambridge, MA 02139 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2002年
/ 124卷
/ 34期
关键词
:
D O I
:
10.1021/ja027466x
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
The first method for the catalytic enantioselective addition of amines (specifically, pyrroles) to ketenes has been developed, and it has been demonstrated that the resulting acylpyrroles can be transformed into a broad spectrum of useful derivatives. On the basis of mechanistic studies, it is suggested that the planar-chiral catalyst plays an unanticipated role in this process as a chiral Brønsted acid. Copyright © 2002 American Chemical Society.
引用
收藏
页码:10006 / 10007
页数:2
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Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
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[J].
JOURNAL OF ORGANIC CHEMISTRY,
1999,
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[2]
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THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY
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Medicinal Chemistry Department, Zeneca Pharmaceuticals, Wilmington, DE 19850-5437
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Houk, KN
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Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
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[J].
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Enantioselective addition of alcohols to ketenes catalyzed by a planar-chiral azaferrocene: Catalytic asymmetric synthesis of arylpropionic acids
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MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
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MIT, Dept Chem, Cambridge, MA 02139 USA
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MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Fu, GC
[J].
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Enantioselective Staudinger synthesis of β-lactams catalyzed by a planar-chiral nucleophile
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MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
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0
h-index:
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MIT, Dept Chem, Cambridge, MA 02139 USA
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Fu, GC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(08)
: 1578
-
1579
←
1
2
3
→
共 24 条
[1]
Amination of ketenes: Kinetic and mechanistic studies
Allen, AD
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
Allen, AD
Tidwell, TT
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
Tidwell, TT
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1999,
64
(01)
: 266
-
271
[2]
Arai S, 2001, ANGEW CHEM INT EDIT, V40, P234, DOI 10.1002/1521-3773(20010105)40:1<234::AID-ANIE234>3.0.CO
[3]
2-K
[4]
Recoverable chiral sulfoxide: Asymmetric Diels-Alder reaction using optically active 1-(2-p-tolysulfinyl)pyrrolyl alpha,beta-unsaturated ketones as a dienophile
Arai, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Gifu Pharmaceutical University, Gifu 502
Arai, Y
Masuda, T
论文数:
0
引用数:
0
h-index:
0
机构:
Gifu Pharmaceutical University, Gifu 502
Masuda, T
Masaki, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Gifu Pharmaceutical University, Gifu 502
Masaki, Y
[J].
CHEMISTRY LETTERS,
1997,
(02)
: 145
-
146
[5]
THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY
BUSCHMANN, H
论文数:
0
引用数:
0
h-index:
0
机构:
Institut für Organische Chemie der Technischen Hochschule, Aachen, W-5100
BUSCHMANN, H
SCHARF, HD
论文数:
0
引用数:
0
h-index:
0
机构:
Institut für Organische Chemie der Technischen Hochschule, Aachen, W-5100
SCHARF, HD
HOFFMANN, N
论文数:
0
引用数:
0
h-index:
0
机构:
Institut für Organische Chemie der Technischen Hochschule, Aachen, W-5100
HOFFMANN, N
ESSER, P
论文数:
0
引用数:
0
h-index:
0
机构:
Institut für Organische Chemie der Technischen Hochschule, Aachen, W-5100
ESSER, P
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
1991,
30
(05)
: 477
-
515
[6]
Addition of transiently-generated methyl o-lithiobenzoate to imines. An isoindolone annulation
Campbell, JB
论文数:
0
引用数:
0
h-index:
0
机构:
Medicinal Chemistry Department, Zeneca Pharmaceuticals, Wilmington, DE 19850-5437
Campbell, JB
Dedinas, RF
论文数:
0
引用数:
0
h-index:
0
机构:
Medicinal Chemistry Department, Zeneca Pharmaceuticals, Wilmington, DE 19850-5437
Dedinas, RF
TrumbowerWalsh, SA
论文数:
0
引用数:
0
h-index:
0
机构:
Medicinal Chemistry Department, Zeneca Pharmaceuticals, Wilmington, DE 19850-5437
TrumbowerWalsh, SA
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1996,
61
(18)
: 6205
-
6211
[7]
The origin of 1,4-asymmetric induction in the additions of chiral alcohols to ketenes
Cannizzaro, CE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Cannizzaro, CE
Strassner, T
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Strassner, T
Houk, KN
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(11)
: 2668
-
2669
[8]
Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed 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
Scheidt, KA
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
Scheidt, KA
Johnston, JN
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
Johnston, JN
Willis, MC
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
Willis, MC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(19)
: 4480
-
4491
[9]
Enantioselective addition of alcohols to ketenes catalyzed by a planar-chiral azaferrocene: Catalytic asymmetric synthesis of arylpropionic acids
Hodous, BL
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Hodous, BL
Ruble, JC
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Ruble, JC
Fu, GC
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Fu, GC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(11)
: 2637
-
2638
[10]
Enantioselective Staudinger synthesis of β-lactams catalyzed by a planar-chiral nucleophile
Hodous, BL
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Hodous, BL
Fu, GC
论文数:
0
引用数:
0
h-index:
0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Fu, GC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(08)
: 1578
-
1579
←
1
2
3
→