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Rate-accelerated nonconventional amide synthesis in water: A practical catalytic aldol-surrogate reaction
被引:115
作者
:
Cho, Seung Hwan
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Dept Chem, CMDS, Taejon 305701, South Korea
Cho, Seung Hwan
Chang, Sukbok
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Dept Chem, CMDS, Taejon 305701, South Korea
Korea Adv Inst Sci & Technol, Dept Chem, CMDS, Taejon 305701, South Korea
Chang, Sukbok
[
1
]
机构
:
[1]
Korea Adv Inst Sci & Technol, Dept Chem, CMDS, Taejon 305701, South Korea
[2]
Korea Adv Inst Sci & Technol, Sch Mol Sci BK21, Taejon 305701, South Korea
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2007年
/ 46卷
/ 11期
关键词
:
beta-hydroxy amides;
alkynes;
azides;
copper;
water;
D O I
:
10.1002/anie.200604358
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) An aldol alternative: Cu-catalyzed hydrative amide synthesis is significantly accelerated in aqueous cosolvent systems. Under environmentally friendly conditions and with N2 released as the single side product, a wide range of propargyl alcohols and sulfonyl azides react to provide β-hydroxy N-sulfonamides in good to excellent yields. Polyhydroxy amides could be synthesized stereoselectively, proving this as a new practical aldol-surrogate strategy. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1897 / 1900
页数:4
相关论文
共 41 条
[1]
Boron-mediated aldol reaction of carboxylic esters
Abiko, A
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 6068585, Japan
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 6068585, Japan
Abiko, A
[J].
ACCOUNTS OF CHEMICAL RESEARCH,
2004,
37
(06)
: 387
-
395
[2]
Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine
Bae, I
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea
Bae, I
Han, H
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea
Han, H
Chang, S
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea
Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea
Chang, S
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(07)
: 2038
-
2039
[3]
Directed methallylations as a synthetic route to 1,3-polyols
Brzezinski, LJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Brzezinski, LJ
Leahy, JW
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Leahy, JW
[J].
TETRAHEDRON LETTERS,
1998,
39
(15)
: 2039
-
2042
[4]
Carreira E. M., 2000, CATALYTIC ASYMMETRIC
[5]
Cassidy M.P., 2006, ANGEW CHEM, V118, P3226
[6]
Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides
Cassidy, Michael P.
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Cassidy, Michael P.
Raushel, Jessica
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Raushel, Jessica
Fokin, Valery V.
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Fokin, Valery V.
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006,
45
(19)
: 3154
-
3157
[7]
Catalytic one-pot synthesis of cyclic amidines by virtue of tandem reactions involving intramolecular hydroamination under mild conditions
Chang, Sukbok
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Chang, Sukbok
Lee, Minjae
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0
引用数:
0
h-index:
0
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Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Lee, Minjae
Jung, Doo Young
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h-index:
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Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Jung, Doo Young
Yoo, Eun Jeong
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Yoo, Eun Jeong
Cho, Seung Hwan
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Cho, Seung Hwan
Han, Sun Kyu
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0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Han, Sun Kyu
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(38)
: 12366
-
12367
[8]
Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water
Cho, SH
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, CMDS, Dept Chem, Taejon 305701, South Korea
Cho, SH
Yoo, EJ
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, CMDS, Dept Chem, Taejon 305701, South Korea
Yoo, EJ
Bae, L
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, CMDS, Dept Chem, Taejon 305701, South Korea
Bae, L
Chang, S
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, CMDS, Dept Chem, Taejon 305701, South Korea
Korea Adv Inst Sci & Technol, CMDS, Dept Chem, Taejon 305701, South Korea
Chang, S
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(46)
: 16046
-
16047
[9]
Novel and efficient synthesis of iminocoumarins via copper-catalyzed multicomponent reaction
Cui, Sun-Liang
论文数:
0
引用数:
0
h-index:
0
机构:
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Cui, Sun-Liang
Lin, Xu-Feng
论文数:
0
引用数:
0
h-index:
0
机构:
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Lin, Xu-Feng
Wang, Yan-Guang
论文数:
0
引用数:
0
h-index:
0
机构:
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Wang, Yan-Guang
[J].
ORGANIC LETTERS,
2006,
8
(20)
: 4517
-
4520
[10]
New strategic reactions for organic synthesis:: Catalytic asymmetric C-H activation α to oxygen as a surrogate to the aldol reaction
Davies, HML
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0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Davies, HML
Beckwith, REJ
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Beckwith, REJ
Antoulinakis, EG
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Antoulinakis, EG
Jin, QH
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Jin, QH
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(16)
: 6126
-
6132
←
1
2
3
4
5
→
共 41 条
[1]
Boron-mediated aldol reaction of carboxylic esters
Abiko, A
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 6068585, Japan
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 6068585, Japan
Abiko, A
[J].
ACCOUNTS OF CHEMICAL RESEARCH,
2004,
37
(06)
: 387
-
395
[2]
Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine
Bae, I
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea
Bae, I
Han, H
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea
Han, H
Chang, S
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea
Korea Adv Inst Sci & Technol, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea
Chang, S
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(07)
: 2038
-
2039
[3]
Directed methallylations as a synthetic route to 1,3-polyols
Brzezinski, LJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Brzezinski, LJ
Leahy, JW
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Leahy, JW
[J].
TETRAHEDRON LETTERS,
1998,
39
(15)
: 2039
-
2042
[4]
Carreira E. M., 2000, CATALYTIC ASYMMETRIC
[5]
Cassidy M.P., 2006, ANGEW CHEM, V118, P3226
[6]
Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides
Cassidy, Michael P.
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Cassidy, Michael P.
Raushel, Jessica
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Raushel, Jessica
Fokin, Valery V.
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Fokin, Valery V.
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006,
45
(19)
: 3154
-
3157
[7]
Catalytic one-pot synthesis of cyclic amidines by virtue of tandem reactions involving intramolecular hydroamination under mild conditions
Chang, Sukbok
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Chang, Sukbok
Lee, Minjae
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Lee, Minjae
Jung, Doo Young
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Jung, Doo Young
Yoo, Eun Jeong
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Yoo, Eun Jeong
Cho, Seung Hwan
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Cho, Seung Hwan
Han, Sun Kyu
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, Ctr Mol Design & Synth, Dept Chem, Taejon 305701, South Korea
Han, Sun Kyu
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(38)
: 12366
-
12367
[8]
Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water
Cho, SH
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, CMDS, Dept Chem, Taejon 305701, South Korea
Cho, SH
Yoo, EJ
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, CMDS, Dept Chem, Taejon 305701, South Korea
Yoo, EJ
Bae, L
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, CMDS, Dept Chem, Taejon 305701, South Korea
Bae, L
Chang, S
论文数:
0
引用数:
0
h-index:
0
机构:
Korea Adv Inst Sci & Technol, CMDS, Dept Chem, Taejon 305701, South Korea
Korea Adv Inst Sci & Technol, CMDS, Dept Chem, Taejon 305701, South Korea
Chang, S
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(46)
: 16046
-
16047
[9]
Novel and efficient synthesis of iminocoumarins via copper-catalyzed multicomponent reaction
Cui, Sun-Liang
论文数:
0
引用数:
0
h-index:
0
机构:
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Cui, Sun-Liang
Lin, Xu-Feng
论文数:
0
引用数:
0
h-index:
0
机构:
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Lin, Xu-Feng
Wang, Yan-Guang
论文数:
0
引用数:
0
h-index:
0
机构:
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
Wang, Yan-Guang
[J].
ORGANIC LETTERS,
2006,
8
(20)
: 4517
-
4520
[10]
New strategic reactions for organic synthesis:: Catalytic asymmetric C-H activation α to oxygen as a surrogate to the aldol reaction
Davies, HML
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Davies, HML
Beckwith, REJ
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Beckwith, REJ
Antoulinakis, EG
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Antoulinakis, EG
Jin, QH
论文数:
0
引用数:
0
h-index:
0
机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
Jin, QH
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(16)
: 6126
-
6132
←
1
2
3
4
5
→