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PdII-catalyzed enantioselective activation of C(sp2)-H and C(sp3)-H bonds using monoprotected amino acids as chiral ligands
被引:526
作者
:
Shi, Bing-Feng
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Shi, Bing-Feng
[
1
]
Maugel, Nathan
论文数:
0
引用数:
0
h-index:
0
机构:
Brandeis Univ, Dept Chem, Waltham, MA 02454 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Maugel, Nathan
[
2
]
Zhang, Yang-Hui
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Zhang, Yang-Hui
[
1
]
Yu, Jin-Quan
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Yu, Jin-Quan
[
1
]
机构
:
[1]
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2]
Brandeis Univ, Dept Chem, Waltham, MA 02454 USA
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2008年
/ 47卷
/ 26期
关键词
:
amino acids;
boronic acids;
C-C coupling;
C-H activation;
enantioselectivity;
D O I
:
10.1002/anie.200801030
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) The relay of chiral information from the α-carbon atom of the amino acid ligand is believed to be crucial for chiral induction in the PdII-catalyzed enantioselective C-H activation/C-C coupling reaction of diphenyl(2-pyridyl)methane with boronic acids (see scheme; BQ=benzoquinone). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4882 / 4886
页数:5
相关论文
共 63 条
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Asymmetric arylation of ketone enolates
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Ahman, J
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MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
Ahman, J
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Palucki, M
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MIT, Dept Chem, Cambridge, MA 02139 USA
MIT, Dept Chem, Cambridge, MA 02139 USA
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
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Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Alberico, Dino
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Scott, Mark E.
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Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
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Lautens, Mark
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Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
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Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides
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MIT, Dept Chem, Cambridge, MA 02139 USA
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MIT, Dept Chem, Cambridge, MA 02139 USA
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.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
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-10483
[4]
A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole→dihydroindoloazocine cyclization
[J].
Baran, PS
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Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
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Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Corey, EJ
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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124
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Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
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Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature
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Boele, MDK
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Univ Amsterdam, Fac Sci, Inst Mol Chem, NL-1018 WV Amsterdam, Netherlands
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Brookhart, Maurice
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Green, Malcolm L. H.
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Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
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Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
Parkin, Gerard
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PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,
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104
(17)
:6908
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SELECTIVITY AND MECHANISM IN CATALYTIC ASYMMETRIC-SYNTHESIS
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BROWN, JM
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0
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.
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22
(01)
:25
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[9]
PALLADIUM-CATALYZED POLYENE CYCLIZATIONS OF TRIENYL TRIFLATES
[J].
CARPENTER, NE
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UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
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UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
OVERMAN, LE
.
JOURNAL OF ORGANIC CHEMISTRY,
1989,
54
(25)
:5846
-5848
[10]
Serial ligand catalysis: A highly selective allylic C-H oxidation
[J].
Chen, MS
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h-index:
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Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Chen, MS
;
Prabagaran, N
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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
Prabagaran, N
;
Labenz, NA
论文数:
0
引用数:
0
h-index:
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机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Labenz, NA
;
White, MC
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h-index:
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机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
White, MC
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(19)
:6970
-6971
←
1
2
3
4
5
6
7
→
共 63 条
[1]
Asymmetric arylation of ketone enolates
[J].
Ahman, J
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
Ahman, J
;
Wolfe, JP
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
Wolfe, JP
;
Troutman, MV
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
Troutman, MV
;
Palucki, M
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
Palucki, M
;
Buchwald, SL
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
Buchwald, SL
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1998,
120
(08)
:1918
-1919
[2]
Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
[J].
Alberico, Dino
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Alberico, Dino
;
Scott, Mark E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Scott, Mark E.
;
Lautens, Mark
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada
Lautens, Mark
.
CHEMICAL REVIEWS,
2007,
107
(01)
:174
-238
[3]
Catalytic enantioselective Negishi reactions of racemic secondary benzylic halides
[J].
Arp, FO
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
Arp, FO
;
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
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(30)
:10482
-10483
[4]
A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole→dihydroindoloazocine cyclization
[J].
Baran, PS
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
Baran, PS
;
Corey, EJ
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
Corey, EJ
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(27)
:7904
-7905
[5]
Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
[6]
Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature
[J].
Boele, MDK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Amsterdam, Fac Sci, Inst Mol Chem, NL-1018 WV Amsterdam, Netherlands
Boele, MDK
;
van Strijdonck, GPF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Amsterdam, Fac Sci, Inst Mol Chem, NL-1018 WV Amsterdam, Netherlands
van Strijdonck, GPF
;
de Vries, AHM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Amsterdam, Fac Sci, Inst Mol Chem, NL-1018 WV Amsterdam, Netherlands
de Vries, AHM
;
Kamer, PCJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Amsterdam, Fac Sci, Inst Mol Chem, NL-1018 WV Amsterdam, Netherlands
Kamer, PCJ
;
de Vries, JG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Amsterdam, Fac Sci, Inst Mol Chem, NL-1018 WV Amsterdam, Netherlands
de Vries, JG
;
van Leeuwen, PWNM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Amsterdam, Fac Sci, Inst Mol Chem, NL-1018 WV Amsterdam, Netherlands
van Leeuwen, PWNM
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(08)
:1586
-1587
[7]
Agostic interactions in transition metal compounds
[J].
Brookhart, Maurice
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
Brookhart, Maurice
;
Green, Malcolm L. H.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
Green, Malcolm L. H.
;
Parkin, Gerard
论文数:
0
引用数:
0
h-index:
0
机构:
Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
Parkin, Gerard
.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,
2007,
104
(17)
:6908
-6914
[8]
SELECTIVITY AND MECHANISM IN CATALYTIC ASYMMETRIC-SYNTHESIS
[J].
BROWN, JM
论文数:
0
引用数:
0
h-index:
0
BROWN, JM
.
CHEMICAL SOCIETY REVIEWS,
1993,
22
(01)
:25
-41
[9]
PALLADIUM-CATALYZED POLYENE CYCLIZATIONS OF TRIENYL TRIFLATES
[J].
CARPENTER, NE
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
CARPENTER, NE
;
KUCERA, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
KUCERA, DJ
;
OVERMAN, LE
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
OVERMAN, LE
.
JOURNAL OF ORGANIC CHEMISTRY,
1989,
54
(25)
:5846
-5848
[10]
Serial ligand catalysis: A highly selective allylic C-H oxidation
[J].
Chen, MS
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
Chen, MS
;
Prabagaran, N
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
Prabagaran, N
;
Labenz, NA
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
Labenz, NA
;
White, 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
White, MC
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(19)
:6970
-6971
←
1
2
3
4
5
6
7
→