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PtCl2-catalyzed cycloisomerizations of 5-En-1-yn-3-ol systems
被引:208
作者
:
Harrak, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Harrak, Y
[
1
]
Blaszykowski, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Blaszykowski, C
[
1
]
Bernard, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Bernard, M
[
1
]
Cariou, K
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Cariou, K
[
1
]
Mainetti, E
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Mainetti, E
[
1
]
Mouriès, V
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Mouriès, V
[
1
]
Dhimane, AL
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Dhimane, AL
[
1
]
Fensterbank, L
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Fensterbank, L
[
1
]
Malacria, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
Malacria, M
[
1
]
机构
:
[1]
Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2004年
/ 126卷
/ 28期
关键词
:
D O I
:
10.1021/ja0474695
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
5-En-1-yn-3-ol substrates bearing a free hydroxyl group or an acyl group are highly versatile partners for PtCl2-catalyzed cycloisomerizations. Electrophilic activation of the alkyne moiety triggers at wish a hydride or an O-acyl migration yielding at the end to regioisomeric keto derivatives. The efficient preparation of Sabina ketone, an important monoterpene precursor, has been worked out. Copyright © 2004 American Chemical Society.
引用
收藏
页码:8656 / 8657
页数:2
相关论文
共 22 条
[1]
The behavior of 1,n-enynes in the presence of transition metals
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Aubert, C
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Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Aubert, C
;
Buisine, O
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0
引用数:
0
h-index:
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机构:
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Buisine, O
;
Malacria, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Malacria, M
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Enantioselective synthesis of sabina ketone
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Barberis, M
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Univ Valencia, ICMOL, Dept Quim Organ, E-46100 Valencia, Spain
Univ Valencia, ICMOL, Dept Quim Organ, E-46100 Valencia, Spain
Barberis, M
;
Pérez-Prieto, J
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0
引用数:
0
h-index:
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机构:
Univ Valencia, ICMOL, Dept Quim Organ, E-46100 Valencia, Spain
Univ Valencia, ICMOL, Dept Quim Organ, E-46100 Valencia, Spain
Pérez-Prieto, J
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PtCl2-catalyzed cycloisomerizations of allenynes
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Cadran, N
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引用数:
0
h-index:
0
机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Cadran, N
;
Cariou, K
论文数:
0
引用数:
0
h-index:
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机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Cariou, K
;
Hervé, G
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0
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Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Hervé, G
;
Aubert, C
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引用数:
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Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Aubert, C
;
Fensterbank, L
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0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Fensterbank, L
;
Malacria, M
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0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Malacria, M
;
Marco-Contelles, J
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0
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Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Marco-Contelles, J
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Construction of novel polycyclic ring systems by transition-metal-catalyzed cycloisomerization of ene-ene-ynes. Interception of a carbenoid intermediate in skeletal reorganization of enynes
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Chatani, N
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Kataoka, K
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Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
Kataoka, K
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Murai, S
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0
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0
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Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
Murai, S
;
Furukawa, N
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0
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0
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Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
Furukawa, N
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Seki, Y
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Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
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Platinum-catalyzed cycloisomerization reactions of enynes
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Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Fürstner, A
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Stelzer, F
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Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Stelzer, F
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Szillat, H
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Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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Platinum- and acid-catalyzed enyne metathesis reactions:: Mechanistic studies and applications to the syntheses of streptorubin B and metacycloprodigiosin
[J].
Fürstner, A
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0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Fürstner, A
;
Szillat, H
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Szillat, H
;
Gabor, B
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h-index:
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机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Gabor, B
;
Mynott, R
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Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
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A short and efficient synthesis of (±)-trans-sabinene hydrate
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Givaudan Flavors Corp, Dept Res & Dev, Organ Chem Sect, Cincinnati, OH 45216 USA
Givaudan Flavors Corp, Dept Res & Dev, Organ Chem Sect, Cincinnati, OH 45216 USA
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Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones
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Kirschberg, T
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CHRISTIAN ALBRECHTS UNIV KIEL, INST ORGAN CHEM, D-24098 KIEL, GERMANY
CHRISTIAN ALBRECHTS UNIV KIEL, INST ORGAN CHEM, D-24098 KIEL, GERMANY
Kirschberg, T
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Mattay, J
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CHRISTIAN ALBRECHTS UNIV KIEL, INST ORGAN CHEM, D-24098 KIEL, GERMANY
CHRISTIAN ALBRECHTS UNIV KIEL, INST ORGAN CHEM, D-24098 KIEL, GERMANY
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Lloyd-Jones, GC
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0
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Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
Lloyd-Jones, GC
.
ORGANIC & BIOMOLECULAR CHEMISTRY,
2003,
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2
3
→
共 22 条
[1]
The behavior of 1,n-enynes in the presence of transition metals
[J].
Aubert, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Aubert, C
;
Buisine, O
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Buisine, O
;
Malacria, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Univ Paris 06, Lab Chim Organ Synth, F-75252 Paris 05, France
Malacria, M
.
CHEMICAL REVIEWS,
2002,
102
(03)
:813
-834
[2]
Enantioselective synthesis of sabina ketone
[J].
Barberis, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Valencia, ICMOL, Dept Quim Organ, E-46100 Valencia, Spain
Univ Valencia, ICMOL, Dept Quim Organ, E-46100 Valencia, Spain
Barberis, M
;
Pérez-Prieto, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Valencia, ICMOL, Dept Quim Organ, E-46100 Valencia, Spain
Univ Valencia, ICMOL, Dept Quim Organ, E-46100 Valencia, Spain
Pérez-Prieto, J
.
TETRAHEDRON LETTERS,
2003,
44
(35)
:6683
-6685
[3]
PtCl2-catalyzed cycloisomerizations of allenynes
[J].
Cadran, N
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Cadran, N
;
Cariou, K
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Cariou, K
;
Hervé, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Hervé, G
;
Aubert, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Aubert, C
;
Fensterbank, L
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Fensterbank, L
;
Malacria, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Malacria, M
;
Marco-Contelles, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Paris 06, Chim Organ Lab, UMR CNRS 7611, F-75252 Paris 05, France
Marco-Contelles, J
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(11)
:3408
-3409
[4]
CHAMAULT L, 2004, CHEM COMMUN, P850
[5]
Construction of novel polycyclic ring systems by transition-metal-catalyzed cycloisomerization of ene-ene-ynes. Interception of a carbenoid intermediate in skeletal reorganization of enynes
[J].
论文数:
引用数:
h-index:
机构:
Chatani, N
;
Kataoka, K
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
Kataoka, K
;
Murai, S
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
Murai, S
;
Furukawa, N
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
Furukawa, N
;
Seki, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
Seki, Y
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1998,
120
(35)
:9104
-9105
[6]
Platinum-catalyzed cycloisomerization reactions of enynes
[J].
Fürstner, A
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Fürstner, A
;
Stelzer, F
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Stelzer, F
;
Szillat, H
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Szillat, H
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(48)
:11863
-11869
[7]
Platinum- and acid-catalyzed enyne metathesis reactions:: Mechanistic studies and applications to the syntheses of streptorubin B and metacycloprodigiosin
[J].
Fürstner, A
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Fürstner, A
;
Szillat, H
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Szillat, H
;
Gabor, B
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Gabor, B
;
Mynott, R
论文数:
0
引用数:
0
h-index:
0
机构:
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
Mynott, R
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1998,
120
(33)
:8305
-8314
[8]
A short and efficient synthesis of (±)-trans-sabinene hydrate
[J].
Galopin, CC
论文数:
0
引用数:
0
h-index:
0
机构:
Givaudan Flavors Corp, Dept Res & Dev, Organ Chem Sect, Cincinnati, OH 45216 USA
Givaudan Flavors Corp, Dept Res & Dev, Organ Chem Sect, Cincinnati, OH 45216 USA
Galopin, CC
.
TETRAHEDRON LETTERS,
2001,
42
(33)
:5589
-5591
[9]
Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones
[J].
Kirschberg, T
论文数:
0
引用数:
0
h-index:
0
机构:
CHRISTIAN ALBRECHTS UNIV KIEL, INST ORGAN CHEM, D-24098 KIEL, GERMANY
CHRISTIAN ALBRECHTS UNIV KIEL, INST ORGAN CHEM, D-24098 KIEL, GERMANY
Kirschberg, T
;
Mattay, J
论文数:
0
引用数:
0
h-index:
0
机构:
CHRISTIAN ALBRECHTS UNIV KIEL, INST ORGAN CHEM, D-24098 KIEL, GERMANY
CHRISTIAN ALBRECHTS UNIV KIEL, INST ORGAN CHEM, D-24098 KIEL, GERMANY
Mattay, J
.
JOURNAL OF ORGANIC CHEMISTRY,
1996,
61
(25)
:8885
-8896
[10]
Mechanistic aspects of transition metal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions
[J].
Lloyd-Jones, GC
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
Lloyd-Jones, GC
.
ORGANIC & BIOMOLECULAR CHEMISTRY,
2003,
1
(02)
:215
-236
←
1
2
3
→