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Enantioselective copper-catalyzed propargylic amination
被引:202
作者
:
Detz, Remko J.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Amsterdam, Vant Hoff Inst Mol Sci Biomol Synth, NL-1018 WS Amsterdam, Netherlands
Univ Amsterdam, Vant Hoff Inst Mol Sci Biomol Synth, NL-1018 WS Amsterdam, Netherlands
Detz, Remko J.
[
1
]
Delville, Marielle M. E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Amsterdam, Vant Hoff Inst Mol Sci Biomol Synth, NL-1018 WS Amsterdam, Netherlands
Univ Amsterdam, Vant Hoff Inst Mol Sci Biomol Synth, NL-1018 WS Amsterdam, Netherlands
Delville, Marielle M. E.
[
1
]
Hiemstra, Henk
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Amsterdam, Vant Hoff Inst Mol Sci Biomol Synth, NL-1018 WS Amsterdam, Netherlands
Univ Amsterdam, Vant Hoff Inst Mol Sci Biomol Synth, NL-1018 WS Amsterdam, Netherlands
Hiemstra, Henk
[
1
]
van Maarseveen, Jan H.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Amsterdam, Vant Hoff Inst Mol Sci Biomol Synth, NL-1018 WS Amsterdam, Netherlands
Univ Amsterdam, Vant Hoff Inst Mol Sci Biomol Synth, NL-1018 WS Amsterdam, Netherlands
van Maarseveen, Jan H.
[
1
]
机构
:
[1]
Univ Amsterdam, Vant Hoff Inst Mol Sci Biomol Synth, NL-1018 WS Amsterdam, Netherlands
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2008年
/ 47卷
/ 20期
关键词
:
amination;
asymmetric catalysis;
P;
N ligands;
propargylic amines;
pybox ligands;
D O I
:
10.1002/anie.200705264
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) A proper copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic acetates with aromatic side chains (R = Ar) into their amine counterparts in high yield and with good selectivity (up to 88% ee). The resulting chiral propargylic amines can be elaborated further into P,N ligands (see scheme; DIPEA = diisopropylethylamine). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3777 / 3780
页数:4
相关论文
共 22 条
[1]
The stereodivergent synthesis of chiral 4,5-disubstituted pybox ligands
[J].
Desimoni, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Desimoni, G
;
Faita, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Faita, G
;
Guala, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Guala, M
;
Pratelli, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Pratelli, C
.
TETRAHEDRON-ASYMMETRY,
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A new and highly efficient catalyst for the enantioselective Mukaiyama-Michael reaction between (E)-3-crotonoyl-1,3-oxazolidin-2-one and 2-trimethylsilyloxyfuran
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Desimoni, G
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Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
Desimoni, G
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Faita, G
论文数:
0
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0
h-index:
0
机构:
Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
Faita, G
;
论文数:
引用数:
h-index:
机构:
Filippone, S
;
Mella, M
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0
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0
h-index:
0
机构:
Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
Mella, M
;
Zampori, MG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
Zampori, MG
;
Zema, M
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0
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0
h-index:
0
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Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
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Clickphine: A novel and highly versatile P,N ligand class via click chemistry
[J].
Detz, Remko J.
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0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
Detz, Remko J.
;
Arevalo Heras, Silvia
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
Arevalo Heras, Silvia
;
de Gelder, R.
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
de Gelder, R.
;
van Leeuwen, Piet W. N. M.
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
van Leeuwen, Piet W. N. M.
;
Hiemstra, Henk
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
Hiemstra, Henk
;
Reek, Joost N. H.
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
Reek, Joost N. H.
;
van Maarseveen, Jan H.
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
van Maarseveen, Jan H.
.
ORGANIC LETTERS,
2006,
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:3227
-3230
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Evans P. A., 2006, ANGEW CHEM, V118, P5092
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Rhodium-catalyzed propargylic substitution: A divergent approach to propargylic and allenyl sulfonamides
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Evans, P. Andrew
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0
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0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Evans, P. Andrew
;
Lawler, Michael J.
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Lawler, Michael J.
.
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2006,
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[6]
Gold(III)-catalyzed nucleophilic substitution of propargylic alcohols
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Georgy, M
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0
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CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
Georgy, M
;
Boucard, V
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
Boucard, V
;
Campagne, JM
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
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C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis
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Ghosh, AK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Ghosh, AK
;
Packiarajan, M
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0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Packiarajan, M
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Cappiello, J
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Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
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Enantioselective oxidation of olefins catalyzed by chiral copper bis(oxazolinyl)pyridine complexes: a reassessment
[J].
Ginotra, SK
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0
引用数:
0
h-index:
0
机构:
Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
Ginotra, SK
;
Singh, VK
论文数:
0
引用数:
0
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Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
Singh, VK
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TETRAHEDRON,
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Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates
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Himo, F
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Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Himo, F
;
Lovell, T
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0
引用数:
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0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Lovell, T
;
Hilgraf, R
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0
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0
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0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Hilgraf, R
;
Rostovtsev, VV
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0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Rostovtsev, VV
;
Noodleman, L
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0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Noodleman, L
;
Sharpless, KB
论文数:
0
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0
h-index:
0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Sharpless, KB
;
Fokin, VV
论文数:
0
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0
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Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
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OSAKA UNIV,FAC ENGN SCI,DEPT CHEM,TOYONAKA,OSAKA 560,JAPAN
OSAKA UNIV,FAC ENGN SCI,DEPT CHEM,TOYONAKA,OSAKA 560,JAPAN
IMADA, Y
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YUASA, M
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0
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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
YUASA, M
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NAKAMURA, I
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0
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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
NAKAMURA, I
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MURAHASHI, S
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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
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共 22 条
[1]
The stereodivergent synthesis of chiral 4,5-disubstituted pybox ligands
[J].
Desimoni, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Desimoni, G
;
Faita, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Faita, G
;
Guala, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Guala, M
;
Pratelli, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
Pratelli, C
.
TETRAHEDRON-ASYMMETRY,
2002,
13
(15)
:1651
-1654
[2]
A new and highly efficient catalyst for the enantioselective Mukaiyama-Michael reaction between (E)-3-crotonoyl-1,3-oxazolidin-2-one and 2-trimethylsilyloxyfuran
[J].
Desimoni, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
Desimoni, G
;
Faita, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
Faita, G
;
论文数:
引用数:
h-index:
机构:
Filippone, S
;
Mella, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
Mella, M
;
Zampori, MG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
Zampori, MG
;
Zema, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
Zema, M
.
TETRAHEDRON,
2001,
57
(51)
:10203
-10212
[3]
Clickphine: A novel and highly versatile P,N ligand class via click chemistry
[J].
Detz, Remko J.
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
Detz, Remko J.
;
Arevalo Heras, Silvia
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
Arevalo Heras, Silvia
;
de Gelder, R.
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
de Gelder, R.
;
van Leeuwen, Piet W. N. M.
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
van Leeuwen, Piet W. N. M.
;
Hiemstra, Henk
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
Hiemstra, Henk
;
Reek, Joost N. H.
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
Reek, Joost N. H.
;
van Maarseveen, Jan H.
论文数:
0
引用数:
0
h-index:
0
机构:
Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
van Maarseveen, Jan H.
.
ORGANIC LETTERS,
2006,
8
(15)
:3227
-3230
[4]
Evans P. A., 2006, ANGEW CHEM, V118, P5092
[5]
Rhodium-catalyzed propargylic substitution: A divergent approach to propargylic and allenyl sulfonamides
[J].
Evans, P. Andrew
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Evans, P. Andrew
;
Lawler, Michael J.
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
Lawler, Michael J.
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006,
45
(30)
:4970
-4972
[6]
Gold(III)-catalyzed nucleophilic substitution of propargylic alcohols
[J].
Georgy, M
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
Georgy, M
;
Boucard, V
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
Boucard, V
;
Campagne, JM
论文数:
0
引用数:
0
h-index:
0
机构:
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
CNRS, Inst Chim Subst Nat, F-91190 Gif Sur Yvette, France
Campagne, JM
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(41)
:14180
-14181
[7]
C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis
[J].
Ghosh, AK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Ghosh, AK
;
Packiarajan, M
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Packiarajan, M
;
Cappiello, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Cappiello, J
.
TETRAHEDRON-ASYMMETRY,
1998,
9
(01)
:1
-45
[8]
Enantioselective oxidation of olefins catalyzed by chiral copper bis(oxazolinyl)pyridine complexes: a reassessment
[J].
Ginotra, SK
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
Ginotra, SK
;
Singh, VK
论文数:
0
引用数:
0
h-index:
0
机构:
Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
Singh, VK
.
TETRAHEDRON,
2006,
62
(15)
:3573
-3581
[9]
Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates
[J].
Himo, F
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Himo, F
;
Lovell, T
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Lovell, T
;
Hilgraf, R
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Hilgraf, R
;
Rostovtsev, VV
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Rostovtsev, VV
;
Noodleman, L
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Noodleman, L
;
Sharpless, KB
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
Sharpless, KB
;
Fokin, VV
论文数:
0
引用数:
0
h-index:
0
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