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Total synthesis of (+)-lepadin B: Stereoselective synthesis of nonracemic polysubstituted hydroquinolines using an RC-ROM process
被引:67
作者
:
Barbe, Guillaume
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Stn Downtown, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Stn Downtown, Montreal, PQ H3C 3J7, Canada
Barbe, Guillaume
[
1
]
Charette, Andre B.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Stn Downtown, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Stn Downtown, Montreal, PQ H3C 3J7, Canada
Charette, Andre B.
[
1
]
机构
:
[1]
Univ Montreal, Dept Chim, Stn Downtown, Montreal, PQ H3C 3J7, Canada
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2008年
/ 130卷
/ 42期
基金
:
加拿大自然科学与工程研究理事会;
关键词
:
D O I
:
10.1021/ja8068215
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
This communication describes a new tandem metathesis reaction for which an RC-ROM mechanism was experimentally supported. This process was successfully applied to the synthesis of cis-fused polyhydroquinolines enabling a short stereoselective total synthesis of ent-lepadin B. Copyright © 2008 American Chemical Society.
引用
收藏
页码:13873 / 13875
页数:3
相关论文
共 52 条
[1]
Domino metathesis of 2-azanorbornenones:: A new strategy for the enatioselective synthesis of 1-azabicyclic compounds
Arjona, O
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Arjona, O
Csáky, AG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Csáky, AG
Medel, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Medel, R
Plumet, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Plumet, J
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2002,
67
(04)
: 1380
-
1383
[2]
Regioselective domino metathesis of 7-oxanorbornene derivatives as a new stereoselective entry into 2,6-dioxabicyclo[4.3.0]nonenes
Arjona, O
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Arjona, O
Csáky, AG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Csáky, AG
Murcia, MC
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Murcia, MC
Plumet, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Plumet, J
[J].
TETRAHEDRON LETTERS,
2000,
41
(50)
: 9777
-
9779
[3]
Azabicycloalkenes as synthetic intermediates -: Synthesis of azabicyclo[X. 3.0] alkane scaffolds
Buechert, Marina
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Buechert, Marina
Meinke, Sebastian
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Meinke, Sebastian
Prenzel, Alexander H. G. P.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Prenzel, Alexander H. G. P.
Deppermann, Nina
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Deppermann, Nina
Maison, Wolfgang
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Maison, Wolfgang
[J].
ORGANIC LETTERS,
2006,
8
(24)
: 5553
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5556
[4]
Electrophilic activation of lactams with Tf2O and pyridine:: Expedient synthesis of (±)-tetraponerine T4
Charette, AB
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Charette, AB
Mathieu, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Mathieu, S
Martel, J
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引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Martel, J
[J].
ORGANIC LETTERS,
2005,
7
(24)
: 5401
-
5404
[5]
Practical and highly regio- and stereoselective synthesis of 2-substituted dihydropyridines and piperidines: Application to the synthesis of (-)-coniine
Charette, AB
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Charette, AB
Grenon, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Grenon, M
Lemire, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Lemire, A
Pourashraf, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Pourashraf, M
Martel, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Martel, J
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(47)
: 11829
-
11830
[6]
OXIDATION REACTIONS USING UREA HYDROGEN-PEROXIDE - A SAFE ALTERNATIVE TO ANHYDROUS HYDROGEN-PEROXIDE
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LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
COOPER, MS
HEANEY, H
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引用数:
0
h-index:
0
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LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
HEANEY, H
NEWBOLD, AJ
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h-index:
0
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LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
NEWBOLD, AJ
SANDERSON, WR
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0
h-index:
0
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LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
SANDERSON, WR
[J].
SYNLETT,
1990,
(09)
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535
[7]
Lepadins F-H, new cis-decahydroquinoline alkaloids from the Australian ascidian Aplidium tabascum
Davis, RA
论文数:
0
引用数:
0
h-index:
0
机构:
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Davis, RA
Carroll, AR
论文数:
0
引用数:
0
h-index:
0
机构:
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Carroll, AR
Quinn, RJ
论文数:
0
引用数:
0
h-index:
0
机构:
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Quinn, RJ
[J].
JOURNAL OF NATURAL PRODUCTS,
2002,
65
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: 454
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457
[8]
Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
Deiters, A
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Deiters, A
Martin, SF
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Martin, SF
[J].
CHEMICAL REVIEWS,
2004,
104
(05)
: 2199
-
2238
[9]
Direct copper(I) iodide dimethyl sulfide catalyzed conjugate addition of alkenyl groups from vinylzirconocene reagents
El-Batta, A
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0
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0
h-index:
0
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San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
El-Batta, A
Hage, TR
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0
引用数:
0
h-index:
0
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San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
Hage, TR
Plotkin, S
论文数:
0
引用数:
0
h-index:
0
机构:
San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
Plotkin, S
Bergdahl, M
论文数:
0
引用数:
0
h-index:
0
机构:
San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
Bergdahl, M
[J].
ORGANIC LETTERS,
2004,
6
(01)
: 107
-
110
[10]
Stereoselective synthesis of pyridinones: Application to the synthesis of (-)-barrenazines
Focken, Thilo
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
Focken, Thilo
Charette, Andre B.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
Charette, Andre B.
[J].
ORGANIC LETTERS,
2006,
8
(14)
: 2985
-
2988
←
1
2
3
4
5
6
→
共 52 条
[1]
Domino metathesis of 2-azanorbornenones:: A new strategy for the enatioselective synthesis of 1-azabicyclic compounds
Arjona, O
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Arjona, O
Csáky, AG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Csáky, AG
Medel, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Medel, R
Plumet, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ, Madrid, Spain
Plumet, J
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2002,
67
(04)
: 1380
-
1383
[2]
Regioselective domino metathesis of 7-oxanorbornene derivatives as a new stereoselective entry into 2,6-dioxabicyclo[4.3.0]nonenes
Arjona, O
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Arjona, O
Csáky, AG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Csáky, AG
Murcia, MC
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Murcia, MC
Plumet, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
Plumet, J
[J].
TETRAHEDRON LETTERS,
2000,
41
(50)
: 9777
-
9779
[3]
Azabicycloalkenes as synthetic intermediates -: Synthesis of azabicyclo[X. 3.0] alkane scaffolds
Buechert, Marina
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Buechert, Marina
Meinke, Sebastian
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Meinke, Sebastian
Prenzel, Alexander H. G. P.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Prenzel, Alexander H. G. P.
Deppermann, Nina
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Deppermann, Nina
Maison, Wolfgang
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany
Maison, Wolfgang
[J].
ORGANIC LETTERS,
2006,
8
(24)
: 5553
-
5556
[4]
Electrophilic activation of lactams with Tf2O and pyridine:: Expedient synthesis of (±)-tetraponerine T4
Charette, AB
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Charette, AB
Mathieu, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Mathieu, S
Martel, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Martel, J
[J].
ORGANIC LETTERS,
2005,
7
(24)
: 5401
-
5404
[5]
Practical and highly regio- and stereoselective synthesis of 2-substituted dihydropyridines and piperidines: Application to the synthesis of (-)-coniine
Charette, AB
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Charette, AB
Grenon, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Grenon, M
Lemire, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Lemire, A
Pourashraf, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Pourashraf, M
Martel, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada
Martel, J
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(47)
: 11829
-
11830
[6]
OXIDATION REACTIONS USING UREA HYDROGEN-PEROXIDE - A SAFE ALTERNATIVE TO ANHYDROUS HYDROGEN-PEROXIDE
COOPER, MS
论文数:
0
引用数:
0
h-index:
0
机构:
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
COOPER, MS
HEANEY, H
论文数:
0
引用数:
0
h-index:
0
机构:
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
HEANEY, H
NEWBOLD, AJ
论文数:
0
引用数:
0
h-index:
0
机构:
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
NEWBOLD, AJ
SANDERSON, WR
论文数:
0
引用数:
0
h-index:
0
机构:
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
LAPORTE RES & DEV,INTEROX RES & DEV,WIDNES,CHESHIRE,ENGLAND
SANDERSON, WR
[J].
SYNLETT,
1990,
(09)
: 533
-
535
[7]
Lepadins F-H, new cis-decahydroquinoline alkaloids from the Australian ascidian Aplidium tabascum
Davis, RA
论文数:
0
引用数:
0
h-index:
0
机构:
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Davis, RA
Carroll, AR
论文数:
0
引用数:
0
h-index:
0
机构:
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Carroll, AR
Quinn, RJ
论文数:
0
引用数:
0
h-index:
0
机构:
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Griffith Univ, AstraZeneca R&D, Brisbane, Qld 4111, Australia
Quinn, RJ
[J].
JOURNAL OF NATURAL PRODUCTS,
2002,
65
(04):
: 454
-
457
[8]
Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
Deiters, A
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Deiters, A
Martin, SF
论文数:
0
引用数:
0
h-index:
0
机构:
N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
Martin, SF
[J].
CHEMICAL REVIEWS,
2004,
104
(05)
: 2199
-
2238
[9]
Direct copper(I) iodide dimethyl sulfide catalyzed conjugate addition of alkenyl groups from vinylzirconocene reagents
El-Batta, A
论文数:
0
引用数:
0
h-index:
0
机构:
San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
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San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
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San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
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San Diego State Univ, Dept Chem, San Diego, CA 92182 USA
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Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
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