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Deuterium-labeling studies establishing stereochemistry at the oxypalladation step in Wacker-type oxidative cyclization of an o-allylphenol
被引:108
作者
:
Hayashi, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
Hayashi, T
[
1
]
Yamasaki, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
Yamasaki, K
[
1
]
Mimura, M
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
Mimura, M
[
1
]
Uozumi, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
Uozumi, Y
[
1
]
机构
:
[1]
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2004年
/ 126卷
/ 10期
关键词
:
D O I
:
10.1021/ja031946m
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
The stereochemical pathway (syn or anti) of the oxypalladation step was studied in the palladium(II)-catalyzed Wacker-type cyclization of stereospecifically deuterated 6-(2-hydroxyphenyl)-3-deuteriocyclohexenes, cis-3-d-1 and trans-3-d-1, giving dihydrobenzofuran derivatives. The stereochemistry was determined to be syn in the reaction catalyzed by a dicationic palladium(II) catalyst generated from Pd(MeCN)4(BF4)2 and (S,S)-ip-boxax in the presence of benzoquinone in methanol, while it is mainly anti in the reaction catalyzed by PdCl2(MeCN)2 in the presence of a chloride ion. Copyright © 2004 American Chemical Society.
引用
收藏
页码:3036 / 3037
页数:2
相关论文
共 31 条
[11]
Stereochemistry of the Wacker reaction: Modes of addition of hydroxide, methoxide, and phenyl at high and low [Cl-]. A study using chirality transfer
Hamed, O
论文数:
0
引用数:
0
h-index:
0
机构:
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
Hamed, O
Thompson, C
论文数:
0
引用数:
0
h-index:
0
机构:
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
Thompson, C
Henry, PM
论文数:
0
引用数:
0
h-index:
0
机构:
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
Henry, PM
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PALLADIUM-CATALYZED CYCLIZATION OF OMEGA-OLEFINIC TOSAMIDES - SYNTHESIS OF NON-AROMATIC NITROGEN-HETEROCYCLES
HEGEDUS, LS
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0
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0
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HEGEDUS, LS
MCKEARIN, JM
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Henry P. M., 2002, Handbook of OrganopalladiumChemistry for Organic Synthesis, V2, P2119
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SUBSTITUENT EFFECTS ON PALLADIUM(II)-CATALYZED ENANTIOSELECTIVE CYCLIZATION OF A SERIES OF 2-(2-BUTENYL)PHENOLS
HOSOKAWA, T
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0
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0
h-index:
0
HOSOKAWA, T
OKUDA, C
论文数:
0
引用数:
0
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OKUDA, C
MURAHASHI, SI
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MURAHASHI, SI
[J].
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CIS-OXYPALLADATION COMPLEXES DERIVED FROM (1R,5R)-2(10),3-PINADIENE AND THEIR UTILIZATION IN PD(II)-CATALYZED ENANTIOSELECTIVE CYCLIZATION OF 2-(TRANS-2-BUTENYL)PHENOLS
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
HOSOKAWA, T
IMADA, Y
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0
引用数:
0
h-index:
0
IMADA, Y
MURAHASHI, SI
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0
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0
MURAHASHI, SI
[J].
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN,
1985,
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REGIOSELECTIVITY OF PALLADIUM(II)-INDUCED INTRAMOLECULAR CYCLIZATION OF 2-(3-METHYL-2-BUTENYL)PHENOL
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
HOSOKAWA, T
YAMASHITA, S
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
YAMASHITA, S
MURAHASHI, SI
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
MURAHASHI, SI
SONODA, A
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
SONODA, A
[J].
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN,
1976,
49
(12)
: 3662
-
3665
[17]
OXIDATIVE CYCLIZATION OF 2-ALLYLPHENOLS BY PALLADIUM(II) ACETATE - CHANGES IN PRODUCT DISTRIBUTION
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Machikaneyama, Toyonaka, Osaka, Japan, 560, Osaka University
HOSOKAWA, T
MIYAGI, S
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Machikaneyama, Toyonaka, Osaka, Japan, 560, Osaka University
MIYAGI, S
MURAHASHI, S
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Machikaneyama, Toyonaka, Osaka, Japan, 560, Osaka University
MURAHASHI, S
SONODA, A
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Machikaneyama, Toyonaka, Osaka, Japan, 560, Osaka University
SONODA, A
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1978,
43
(14)
: 2752
-
2757
[18]
PALLADIUM(II)-CATALYZED ASYMMETRIC OXIDATIVE CYCLIZATION OF 2-ALLYLPHENOLS IN THE PRESENCE OF COPPER(II) ACETATE AND MOLECULAR-OXYGEN - STUDY OF THE CATALYSIS OF THE WACKER-TYPE OXIDATION
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
HOSOKAWA, T
UNO, T
论文数:
0
引用数:
0
h-index:
0
UNO, T
INUI, S
论文数:
0
引用数:
0
h-index:
0
INUI, S
MURAHASHI, SI
论文数:
0
引用数:
0
h-index:
0
MURAHASHI, SI
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1981,
103
(09)
: 2318
-
2323
[19]
PALLADIUM(II) CATALYZED OLEFIN CARBONYLATION REACTION - STEREOCHEMISTRY OF METHOXYPALLADATION
JAMES, DE
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
JAMES, DE
HINES, LF
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
HINES, LF
STILLE, JK
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
STILLE, JK
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1976,
98
(07)
: 1806
-
1809
[20]
Development, synthetic scope, and mechanistic studies of the palladium-catalyzed cycloisomerization of functionalized 1,6-dienes in the presence of silane
Kisanga, P
论文数:
0
引用数:
0
h-index:
0
机构:
Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
Kisanga, P
Widenhoefer, RA
论文数:
0
引用数:
0
h-index:
0
机构:
Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
Widenhoefer, RA
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(41)
: 10017
-
10026
←
1
2
3
4
→
共 31 条
[11]
Stereochemistry of the Wacker reaction: Modes of addition of hydroxide, methoxide, and phenyl at high and low [Cl-]. A study using chirality transfer
Hamed, O
论文数:
0
引用数:
0
h-index:
0
机构:
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
Hamed, O
Thompson, C
论文数:
0
引用数:
0
h-index:
0
机构:
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
Thompson, C
Henry, PM
论文数:
0
引用数:
0
h-index:
0
机构:
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
LOYOLA UNIV,DEPT CHEM,CHICAGO,IL 60626
Henry, PM
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1997,
62
(21)
: 7082
-
7083
[12]
PALLADIUM-CATALYZED CYCLIZATION OF OMEGA-OLEFINIC TOSAMIDES - SYNTHESIS OF NON-AROMATIC NITROGEN-HETEROCYCLES
HEGEDUS, LS
论文数:
0
引用数:
0
h-index:
0
HEGEDUS, LS
MCKEARIN, JM
论文数:
0
引用数:
0
h-index:
0
MCKEARIN, JM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1982,
104
(09)
: 2444
-
2451
[13]
Henry P. M., 2002, Handbook of OrganopalladiumChemistry for Organic Synthesis, V2, P2119
[14]
SUBSTITUENT EFFECTS ON PALLADIUM(II)-CATALYZED ENANTIOSELECTIVE CYCLIZATION OF A SERIES OF 2-(2-BUTENYL)PHENOLS
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
HOSOKAWA, T
OKUDA, C
论文数:
0
引用数:
0
h-index:
0
OKUDA, C
MURAHASHI, SI
论文数:
0
引用数:
0
h-index:
0
MURAHASHI, SI
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1985,
50
(08)
: 1282
-
1287
[15]
CIS-OXYPALLADATION COMPLEXES DERIVED FROM (1R,5R)-2(10),3-PINADIENE AND THEIR UTILIZATION IN PD(II)-CATALYZED ENANTIOSELECTIVE CYCLIZATION OF 2-(TRANS-2-BUTENYL)PHENOLS
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
HOSOKAWA, T
IMADA, Y
论文数:
0
引用数:
0
h-index:
0
IMADA, Y
MURAHASHI, SI
论文数:
0
引用数:
0
h-index:
0
MURAHASHI, SI
[J].
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN,
1985,
58
(11)
: 3282
-
3290
[16]
REGIOSELECTIVITY OF PALLADIUM(II)-INDUCED INTRAMOLECULAR CYCLIZATION OF 2-(3-METHYL-2-BUTENYL)PHENOL
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
HOSOKAWA, T
YAMASHITA, S
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
YAMASHITA, S
MURAHASHI, SI
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
MURAHASHI, SI
SONODA, A
论文数:
0
引用数:
0
h-index:
0
机构:
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
OSAKA UNIV, FAC ENGN SCI, DEPT CHEM, TOYONAKA, OSAKA 560, JAPAN
SONODA, A
[J].
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN,
1976,
49
(12)
: 3662
-
3665
[17]
OXIDATIVE CYCLIZATION OF 2-ALLYLPHENOLS BY PALLADIUM(II) ACETATE - CHANGES IN PRODUCT DISTRIBUTION
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Machikaneyama, Toyonaka, Osaka, Japan, 560, Osaka University
HOSOKAWA, T
MIYAGI, S
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Machikaneyama, Toyonaka, Osaka, Japan, 560, Osaka University
MIYAGI, S
MURAHASHI, S
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Machikaneyama, Toyonaka, Osaka, Japan, 560, Osaka University
MURAHASHI, S
SONODA, A
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Faculty of Engineering Science, Machikaneyama, Toyonaka, Osaka, Japan, 560, Osaka University
SONODA, A
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1978,
43
(14)
: 2752
-
2757
[18]
PALLADIUM(II)-CATALYZED ASYMMETRIC OXIDATIVE CYCLIZATION OF 2-ALLYLPHENOLS IN THE PRESENCE OF COPPER(II) ACETATE AND MOLECULAR-OXYGEN - STUDY OF THE CATALYSIS OF THE WACKER-TYPE OXIDATION
HOSOKAWA, T
论文数:
0
引用数:
0
h-index:
0
HOSOKAWA, T
UNO, T
论文数:
0
引用数:
0
h-index:
0
UNO, T
INUI, S
论文数:
0
引用数:
0
h-index:
0
INUI, S
MURAHASHI, SI
论文数:
0
引用数:
0
h-index:
0
MURAHASHI, SI
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1981,
103
(09)
: 2318
-
2323
[19]
PALLADIUM(II) CATALYZED OLEFIN CARBONYLATION REACTION - STEREOCHEMISTRY OF METHOXYPALLADATION
JAMES, DE
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
JAMES, DE
HINES, LF
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
HINES, LF
STILLE, JK
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242
STILLE, JK
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1976,
98
(07)
: 1806
-
1809
[20]
Development, synthetic scope, and mechanistic studies of the palladium-catalyzed cycloisomerization of functionalized 1,6-dienes in the presence of silane
Kisanga, P
论文数:
0
引用数:
0
h-index:
0
机构:
Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
Kisanga, P
Widenhoefer, RA
论文数:
0
引用数:
0
h-index:
0
机构:
Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
Widenhoefer, RA
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(41)
: 10017
-
10026
←
1
2
3
4
→