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Decarbonylative cross-coupling of cyclic anhydrides:: Introducing stereochemistry at an sp3 carbon in the cross-coupling event
被引:99
作者
:
O'Brien, EM
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
O'Brien, EM
[
1
]
Bercot, EA
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Bercot, EA
[
1
]
Rovis, T
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Rovis, T
[
1
]
机构
:
[1]
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2003年
/ 125卷
/ 35期
关键词
:
D O I
:
10.1021/ja036290b
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
Treatment of cyclic anhydrides with stoichiometric amounts of nickel-neocuproine complex generates alkylcarboxylato-nickelalactones upon extrusion of CO. These metalacycles undergo cross-coupling with arylzinc reagents. The generated CO is sequestered in situ by a nickel-dppb complex. The overall sequence effects a secondary sp3(electrophile)-sp2(nucleophile) cross-coupling and allows for control of stereochemistry during the bond-forming event. Copyright © 2003 American Chemical Society.
引用
收藏
页码:10498 / 10499
页数:2
相关论文
共 37 条
[1]
A mild and efficient catalytic alkylative monofunctionalization of cyclic anhydrides
Bercot, EA
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Bercot, EA
Rovis, T
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Rovis, T
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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Palladium catalyzed stereoselective cross-couplings and acylations of chiral secondary diorganozincs
Boudier, A
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0
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0
h-index:
0
机构:
Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
Boudier, A
Knochel, P
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
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机构:
Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
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机构:
UNIV AUTONOMA MADRID,DEPT QUIM ORGAN,E-28049 MADRID,SPAIN
CASTANO, AM
ECHAVARREN, AM
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机构:
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
CASTANO, AM
ECHAVARREN, AM
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0
引用数:
0
h-index:
0
机构:
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
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CASTANO, AM
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0
引用数:
0
h-index:
0
机构:
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
CASTANO, AM
ECHAVARREN, AM
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
ECHAVARREN, AM
[J].
TETRAHEDRON LETTERS,
1993,
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Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO
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2-N
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Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[10]
METALLACYCLIC ACYL CARBOXYLATES OF NICKEL - REACTIVITY OF THE ACYL GROUP AND POSSIBLE SYNTHESIS IN CROSS-COUPLING REACTIONS WITH ALKYLHALIDES
FISCHER, R
论文数:
0
引用数:
0
h-index:
0
机构:
FRIEDRICH SCHILLER UNIV,INST ANORGAN & ANALYT CHEM,O-6900 JENA,GERMANY
FISCHER, R
WALTHER, D
论文数:
0
引用数:
0
h-index:
0
机构:
FRIEDRICH SCHILLER UNIV,INST ANORGAN & ANALYT CHEM,O-6900 JENA,GERMANY
WALTHER, D
KEMPE, R
论文数:
0
引用数:
0
h-index:
0
机构:
FRIEDRICH SCHILLER UNIV,INST ANORGAN & ANALYT CHEM,O-6900 JENA,GERMANY
KEMPE, R
SIELER, J
论文数:
0
引用数:
0
h-index:
0
机构:
FRIEDRICH SCHILLER UNIV,INST ANORGAN & ANALYT CHEM,O-6900 JENA,GERMANY
SIELER, J
SCHONECKER, B
论文数:
0
引用数:
0
h-index:
0
机构:
FRIEDRICH SCHILLER UNIV,INST ANORGAN & ANALYT CHEM,O-6900 JENA,GERMANY
SCHONECKER, B
[J].
JOURNAL OF ORGANOMETALLIC CHEMISTRY,
1993,
447
(01)
: 131
-
136
←
1
2
3
4
→
共 37 条
[1]
A mild and efficient catalytic alkylative monofunctionalization of cyclic anhydrides
Bercot, EA
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Bercot, EA
Rovis, T
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Rovis, T
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(02)
: 174
-
175
[2]
Palladium catalyzed stereoselective cross-couplings and acylations of chiral secondary diorganozincs
Boudier, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
Boudier, A
Knochel, P
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
Knochel, P
[J].
TETRAHEDRON LETTERS,
1999,
40
(04)
: 687
-
690
[3]
Advances in functional-group-tolerant metal-catalyzed alkyl-alkyl cross-coupling reactions
Cárdenas, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
Cárdenas, DJ
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2003,
42
(04)
: 384
-
387
[4]
REACTIVITY OF NICKELACYCLE DERIVED FROM ASPARTIC-ACID - ALKYLATIONS, INSERTIONS, AND OXIDATIONS
CASTANO, AM
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV AUTONOMA MADRID,DEPT QUIM ORGAN,E-28049 MADRID,SPAIN
CASTANO, AM
ECHAVARREN, AM
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV AUTONOMA MADRID,DEPT QUIM ORGAN,E-28049 MADRID,SPAIN
ECHAVARREN, AM
[J].
ORGANOMETALLICS,
1994,
13
(06)
: 2262
-
2268
[5]
REGIOSELECTIVE FUNCTIONALIZATION OF CHIRAL NICKELACYCLES DERIVED FROM N-PROTECTED ASPARTIC AND GLUTAMIC ANHYDRIDES
CASTANO, AM
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
CASTANO, AM
ECHAVARREN, AM
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
ECHAVARREN, AM
[J].
TETRAHEDRON LETTERS,
1990,
31
(33)
: 4783
-
4786
[6]
SYNTHESIS OF PROTECTED 3-METHYLASPARTIC ACIDS FROM GLUTAMIC ANHYDRIDE VIA NICKELACYCLES
CASTANO, AM
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
CASTANO, AM
ECHAVARREN, AM
论文数:
0
引用数:
0
h-index:
0
机构:
CSIC,INST QUIM ORGAN,JUAN CIERVA 3,E-28006 MADRID,SPAIN
ECHAVARREN, AM
[J].
TETRAHEDRON LETTERS,
1993,
34
(27)
: 4361
-
4362
[7]
Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO
[8]
2-N
[9]
Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[10]
METALLACYCLIC ACYL CARBOXYLATES OF NICKEL - REACTIVITY OF THE ACYL GROUP AND POSSIBLE SYNTHESIS IN CROSS-COUPLING REACTIONS WITH ALKYLHALIDES
FISCHER, R
论文数:
0
引用数:
0
h-index:
0
机构:
FRIEDRICH SCHILLER UNIV,INST ANORGAN & ANALYT CHEM,O-6900 JENA,GERMANY
FISCHER, R
WALTHER, D
论文数:
0
引用数:
0
h-index:
0
机构:
FRIEDRICH SCHILLER UNIV,INST ANORGAN & ANALYT CHEM,O-6900 JENA,GERMANY
WALTHER, D
KEMPE, R
论文数:
0
引用数:
0
h-index:
0
机构:
FRIEDRICH SCHILLER UNIV,INST ANORGAN & ANALYT CHEM,O-6900 JENA,GERMANY
KEMPE, R
SIELER, J
论文数:
0
引用数:
0
h-index:
0
机构:
FRIEDRICH SCHILLER UNIV,INST ANORGAN & ANALYT CHEM,O-6900 JENA,GERMANY
SIELER, J
SCHONECKER, B
论文数:
0
引用数:
0
h-index:
0
机构:
FRIEDRICH SCHILLER UNIV,INST ANORGAN & ANALYT CHEM,O-6900 JENA,GERMANY
SCHONECKER, B
[J].
JOURNAL OF ORGANOMETALLIC CHEMISTRY,
1993,
447
(01)
: 131
-
136
←
1
2
3
4
→