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Ni(II) Tol-BINAP-catalyzed enantioselective Michael reactions of β-ketoesters and unsaturated N-acylthiazolidinethiones
被引:60
作者
:
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
[
1
]
Thomson, RJ
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Thomson, RJ
[
1
]
Franco, F
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Franco, F
[
1
]
机构
:
[1]
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2005年
/ 127卷
/ 31期
关键词
:
D O I
:
10.1021/ja053820q
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
The enantioselective addition of β-ketoesters to unsaturated N-acylthiazolidinethiones catalyzed by Ni(II) Tol-BINAP Lewis acid complexes is reported. Notable features of this reaction are its operation simplicity, the obviated need for the addition of an external base, and the ease with which the adducts are converted into a range of potentially useful derivatives. In particular, the dihydropyrone adducts are versatile scaffolds for further stereoselective elaboration. Copyright © 2005 American Chemical Society.
引用
收藏
页码:10816 / 10817
页数:2
相关论文
共 22 条
[1]
ASYMMETRIC-SYNTHESIS OF BETA-SUBSTITUTED DELTA-KETOESTERS VIA MICHAEL-ADDITIONS OF SAMP RAMP-HYDRAZONES TO ALPHA,BETA-UNSATURATED ESTERS, VIRTUALLY COMPLETE 1,6-ASYMMETRIC INDUCTION
[J].
ENDERS, D
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0
引用数:
0
h-index:
0
ENDERS, D
;
PAPADOPOULOS, K
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0
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0
h-index:
0
PAPADOPOULOS, K
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TETRAHEDRON LETTERS,
1983,
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-4970
[2]
Ni(II)-bis[(R,R)-N,N′-dibenzylcyclohexane-1,2-diamine]Br2 catalyzed enantioselective Michael additions of 1,3-dicarbonyl compounds to conjugated nitroalkenes
[J].
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
;
Seidel, D
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Seidel, D
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(28)
:9958
-9959
[3]
Chiral bis(oxazoline)copper(II) complexes as Lewis acid catalysts for the enantioselective Diels-Alder reaction
[J].
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
;
Miller, SJ
论文数:
0
引用数:
0
h-index:
0
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Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Miller, SJ
;
Lectka, T
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Lectka, T
;
von Matt, P
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
von Matt, P
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(33)
:7559
-7573
[4]
Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed by bis(oxazoline) Copper(II) complexes
[J].
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
;
Scheidt, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Scheidt, KA
;
Johnston, JN
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0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Johnston, JN
;
Willis, MC
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0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Willis, MC
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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123
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[5]
Enantioselective Lewis acid catalyzed Michael reactions of alkylidene malonates.: Catalysis by C2-symmetric bis(oxazoline) copper(II) complexes in the synthesis of chiral, differentiated glutarate esters
[J].
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
;
Rovis, T
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Rovis, T
;
Kozlowski, MC
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Kozlowski, MC
;
Downey, CW
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引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Downey, CW
;
Tedrow, JS
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0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Tedrow, JS
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(38)
:9134
-9142
[6]
EVANS DA, 2005, J AM CHEM SOC, V127, P10474
[7]
Asymmetric hydrogenation of substituted 2-pyrones
[J].
Fehr, MJ
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0
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0
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ETH Zentrum, Dept Ind & Engn Chem, Swiss Fed Inst Technol, CH-8092 Zurich, Switzerland
Fehr, MJ
;
Consiglio, G
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0
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0
h-index:
0
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ETH Zentrum, Dept Ind & Engn Chem, Swiss Fed Inst Technol, CH-8092 Zurich, Switzerland
ETH Zentrum, Dept Ind & Engn Chem, Swiss Fed Inst Technol, CH-8092 Zurich, Switzerland
Consiglio, G
;
Scalone, M
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0
引用数:
0
h-index:
0
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ETH Zentrum, Dept Ind & Engn Chem, Swiss Fed Inst Technol, CH-8092 Zurich, Switzerland
Scalone, M
;
Schmid, R
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0
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0
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0
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ETH Zentrum, Dept Ind & Engn Chem, Swiss Fed Inst Technol, CH-8092 Zurich, Switzerland
Schmid, R
.
JOURNAL OF ORGANIC CHEMISTRY,
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64
(16)
:5768
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[8]
A short, efficient synthesis of monofluoro ketomethylene peptide isostere core units
[J].
Hoffman, RV
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Dept. of Chemistry and Biochemistry, New Mexico State University, Las Cruces
Hoffman, RV
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Saenz, JE
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TETRAHEDRON LETTERS,
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38
(49)
:8469
-8472
[9]
Enantioselective enol lactone synthesis under double catalytic conditions
[J].
Itoh, K
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Kyushu Univ, Grad Sch Engn, Dept Mol & Mat Sci, Kasuga, Fukuoka 8168580, Japan
Itoh, K
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Hasegawa, M
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Kyushu Univ, Grad Sch Engn, Dept Mol & Mat Sci, Kasuga, Fukuoka 8168580, Japan
Hasegawa, M
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Tanaka, J
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Tanaka, J
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Kanemasa, S
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h-index:
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Kyushu Univ, Grad Sch Engn, Dept Mol & Mat Sci, Kasuga, Fukuoka 8168580, Japan
Kanemasa, S
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ORGANIC LETTERS,
2005,
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:979
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[10]
Enantioselective Michael addition reactions of malononitrile catalyzed by chiral Lewis acid and achiral amine catalysts
[J].
Itoh, K
论文数:
0
引用数:
0
h-index:
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机构:
Kyushu Univ, JST, CREST, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan
Itoh, K
;
Oderaotoshi, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, JST, CREST, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan
Oderaotoshi, Y
;
Kanemasa, S
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, JST, CREST, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan
Kanemasa, S
.
TETRAHEDRON-ASYMMETRY,
2003,
14
(06)
:635
-639
←
1
2
3
→
共 22 条
[1]
ASYMMETRIC-SYNTHESIS OF BETA-SUBSTITUTED DELTA-KETOESTERS VIA MICHAEL-ADDITIONS OF SAMP RAMP-HYDRAZONES TO ALPHA,BETA-UNSATURATED ESTERS, VIRTUALLY COMPLETE 1,6-ASYMMETRIC INDUCTION
[J].
ENDERS, D
论文数:
0
引用数:
0
h-index:
0
ENDERS, D
;
PAPADOPOULOS, K
论文数:
0
引用数:
0
h-index:
0
PAPADOPOULOS, K
.
TETRAHEDRON LETTERS,
1983,
24
(45)
:4967
-4970
[2]
Ni(II)-bis[(R,R)-N,N′-dibenzylcyclohexane-1,2-diamine]Br2 catalyzed enantioselective Michael additions of 1,3-dicarbonyl compounds to conjugated nitroalkenes
[J].
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
;
Seidel, D
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Seidel, D
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(28)
:9958
-9959
[3]
Chiral bis(oxazoline)copper(II) complexes as Lewis acid catalysts for the enantioselective Diels-Alder reaction
[J].
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
;
Miller, SJ
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Miller, SJ
;
Lectka, T
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Lectka, T
;
von Matt, P
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
von Matt, P
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1999,
121
(33)
:7559
-7573
[4]
Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed by bis(oxazoline) Copper(II) complexes
[J].
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
;
Scheidt, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Scheidt, KA
;
Johnston, JN
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Johnston, JN
;
Willis, MC
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Willis, MC
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(19)
:4480
-4491
[5]
Enantioselective Lewis acid catalyzed Michael reactions of alkylidene malonates.: Catalysis by C2-symmetric bis(oxazoline) copper(II) complexes in the synthesis of chiral, differentiated glutarate esters
[J].
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
;
Rovis, T
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Rovis, T
;
Kozlowski, MC
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Kozlowski, MC
;
Downey, CW
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Downey, CW
;
Tedrow, JS
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Tedrow, JS
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(38)
:9134
-9142
[6]
EVANS DA, 2005, J AM CHEM SOC, V127, P10474
[7]
Asymmetric hydrogenation of substituted 2-pyrones
[J].
Fehr, MJ
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zentrum, Dept Ind & Engn Chem, Swiss Fed Inst Technol, CH-8092 Zurich, Switzerland
Fehr, MJ
;
Consiglio, G
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zentrum, Dept Ind & Engn Chem, Swiss Fed Inst Technol, CH-8092 Zurich, Switzerland
ETH Zentrum, Dept Ind & Engn Chem, Swiss Fed Inst Technol, CH-8092 Zurich, Switzerland
Consiglio, G
;
Scalone, M
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zentrum, Dept Ind & Engn Chem, Swiss Fed Inst Technol, CH-8092 Zurich, Switzerland
Scalone, M
;
Schmid, R
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zentrum, Dept Ind & Engn Chem, Swiss Fed Inst Technol, CH-8092 Zurich, Switzerland
Schmid, R
.
JOURNAL OF ORGANIC CHEMISTRY,
1999,
64
(16)
:5768
-5776
[8]
A short, efficient synthesis of monofluoro ketomethylene peptide isostere core units
[J].
Hoffman, RV
论文数:
0
引用数:
0
h-index:
0
机构:
Dept. of Chemistry and Biochemistry, New Mexico State University, Las Cruces
Hoffman, RV
;
Saenz, JE
论文数:
0
引用数:
0
h-index:
0
机构:
Dept. of Chemistry and Biochemistry, New Mexico State University, Las Cruces
Saenz, JE
.
TETRAHEDRON LETTERS,
1997,
38
(49)
:8469
-8472
[9]
Enantioselective enol lactone synthesis under double catalytic conditions
[J].
Itoh, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Grad Sch Engn, Dept Mol & Mat Sci, Kasuga, Fukuoka 8168580, Japan
Itoh, K
;
Hasegawa, M
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Grad Sch Engn, Dept Mol & Mat Sci, Kasuga, Fukuoka 8168580, Japan
Hasegawa, M
;
Tanaka, J
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Grad Sch Engn, Dept Mol & Mat Sci, Kasuga, Fukuoka 8168580, Japan
Tanaka, J
;
Kanemasa, S
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Grad Sch Engn, Dept Mol & Mat Sci, Kasuga, Fukuoka 8168580, Japan
Kanemasa, S
.
ORGANIC LETTERS,
2005,
7
(06)
:979
-981
[10]
Enantioselective Michael addition reactions of malononitrile catalyzed by chiral Lewis acid and achiral amine catalysts
[J].
Itoh, K
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, JST, CREST, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan
Itoh, K
;
Oderaotoshi, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, JST, CREST, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan
Oderaotoshi, Y
;
Kanemasa, S
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, JST, CREST, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan
Kanemasa, S
.
TETRAHEDRON-ASYMMETRY,
2003,
14
(06)
:635
-639
←
1
2
3
→