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Direct, iridium-catalyzed enantioselective and regioselective allylic etherification with aliphatic alcohols
被引:103
作者
:
Ueno, Satoshi
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Ueno, Satoshi
[
1
]
Hartwig, John F.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
Hartwig, John F.
[
1
]
机构
:
[1]
Univ Illinois, Dept Chem, Urbana, IL 61801 USA
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2008年
/ 47卷
/ 10期
关键词
:
alkoxides;
allylic substitution;
asymmetric synthesis iridium;
metallacycle;
D O I
:
10.1002/anie.200705267
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) From alcohol to ether: Iridium-catalyzed allylations yield α chiral ether derivatives directly from aliphatic alcohols with a simple alkali metal base (see equation). These reactions form ethers from primary, secondary, and tertiary alkoxides with high enantioselectivity. By-products from isomerization were suppressed by the use of an alkyne additive. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1928 / 1931
页数:4
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Effects of catalyst activation and ligand steric properties on the enantioselective allylation of amines and phenoxides
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共 49 条
[11]
Stereoselective palladium-catalyzed O-glycosylation using glycals
[J].
Kim, H
论文数:
0
引用数:
0
h-index:
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;
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[12]
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[J].
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[J].
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0
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0
h-index:
0
机构:
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;
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论文数:
0
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Hartwig, JF
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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127
(44)
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-15514
[14]
Effects of catalyst activation and ligand steric properties on the enantioselective allylation of amines and phenoxides
[J].
Leitner, A
论文数:
0
引用数:
0
h-index:
0
机构:
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Yale Univ, Dept Chem, New Haven, CT 06520 USA
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;
Shu, CT
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0
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0
h-index:
0
机构:
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Yale Univ, Dept Chem, New Haven, CT 06520 USA
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;
Hartwig, JF
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Hartwig, JF
.
ORGANIC LETTERS,
2005,
7
(06)
:1093
-1096
[15]
Editing the stereochemical elements in an iridium catalyst for enantioselective allylic amination
[J].
Leitner, A
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Leitner, A
;
Shu, CT
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Shu, CT
;
Hartwig, JF
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Hartwig, JF
.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,
2004,
101
(16)
:5830
-5833
[16]
Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides
[J].
López, F
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
Yale Univ, Dept Chem, New Haven, CT 06520 USA
López, F
;
Ohmura, T
论文数:
0
引用数:
0
h-index:
0
机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
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Ohmura, T
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h-index:
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机构:
Yale Univ, Dept Chem, New Haven, CT 06520 USA
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Hartwig, JF
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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125
(12)
:3426
-3427
[17]
Lyothier I., 2006, ANGEW CHEM, V118, P6350
[18]
Iridium-catalyzed enantioselective synthesis of allylic alcohols: Silanolates as hydroxide equivalents
[J].
Lyothier, Isabelle
论文数:
0
引用数:
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h-index:
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机构:
ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
Lyothier, Isabelle
;
Defieber, Christian
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引用数:
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h-index:
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机构:
ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
Defieber, Christian
;
Carreira, Erick M.
论文数:
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引用数:
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h-index:
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机构:
ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
Carreira, Erick M.
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006,
45
(37)
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-6207
[19]
First enantioselective allylic etherification with phenols catalyzed by chiral ruthenium bisoxazoline complexes
[J].
Mbaye, MD
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h-index:
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Univ Rennes 1, Inst Chim, UMR 6509, F-35042 Rennes, France
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Mbaye, MD
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h-index:
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Univ Rennes 1, Inst Chim, UMR 6509, F-35042 Rennes, France
Univ Rennes 1, Inst Chim, UMR 6509, F-35042 Rennes, France
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Univ Rennes 1, Inst Chim, UMR 6509, F-35042 Rennes, France
Univ Rennes 1, Inst Chim, UMR 6509, F-35042 Rennes, France
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CHEMICAL COMMUNICATIONS,
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Hydroxylamines as oxygen atom nucleophiles in transition-metal-catalyzed allylic substitution
[J].
Miyabe, H
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h-index:
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机构:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Miyabe, H
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Yoshida, K
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Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Yoshida, K
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引用数:
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h-index:
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机构:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Yamauchi, M
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Takemoto, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
Takemoto, Y
.
JOURNAL OF ORGANIC CHEMISTRY,
2005,
70
(06)
:2148
-2153
←
1
2
3
4
5
→