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Catalytic Asymmetric Bromoamination of Chalcones: Highly Efficient Synthesis of Chiral α-Bromo-β-Amino Ketone Derivatives
被引:159
作者
:
Cai, Yunfei
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Cai, Yunfei
[
1
]
Liu, Xiaohua
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Liu, Xiaohua
[
1
]
Hui, Yonghai
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Hui, Yonghai
[
1
]
Jiang, Jun
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Jiang, Jun
[
1
]
Wang, Wentao
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Wang, Wentao
[
1
]
Chen, Weiliang
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Chen, Weiliang
[
1
]
Lin, Lili
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Lin, Lili
[
1
]
Feng, Xiaoming
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Feng, Xiaoming
[
1
]
机构
:
[1]
Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2010年
/ 49卷
/ 35期
基金
:
中国国家自然科学基金;
关键词
:
asymmetric catalysis;
bromoamination;
chalcones;
scandium;
sulfonamides;
FRIEDEL-CRAFTS ALKYLATION;
STEREOSELECTIVE AMINOBROMINATION;
CONJUGATED DIENES;
OLEFINS;
DIAMINATION;
ALDEHYDES;
NITROGEN;
INDOLES;
TSNH2;
SCOPE;
D O I
:
10.1002/anie.201002355
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
Stand and deliver: The first highly regio- and enantioselective bromoamination of chalcones has been developed which proceeds via an unusual bromonium-based mechanism to deliver the title compounds. Excellent results were obtained using 0.05 mol % of the C2-symmetric N,N'-dioxide/scandium(III) complex under mild conditions (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6160 / 6164
页数:5
相关论文
共 33 条
[1]
Amatore M., 2009, Angew. Chem, V121, P5223
[2]
Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation
Amatore, Muriel
论文数:
0
引用数:
0
h-index:
0
机构:
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Amatore, Muriel
Beeson, Teresa D.
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0
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0
h-index:
0
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Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Beeson, Teresa D.
Brown, Sean P.
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0
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0
h-index:
0
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Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Brown, Sean P.
MacMillan, David W. C.
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0
h-index:
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Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
MacMillan, David W. C.
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Brown, RS
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Department of Chemistry, Queen's University, Kingston
Brown, RS
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Cardona F, 2009, NAT CHEM, V1, P269, DOI [10.1038/nchem.256, 10.1038/NCHEM.256]
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Aluminium Powder-Catalyzed Regio- and Stereoselective Aminobromination of α,β-Unsaturated Carbonyl Compounds and Simple Olefins with the p-Toluenesulfonamide/N-Bromosuccinimide (TsNH2-NBS) System
Chen, Zhan-Guo
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0
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Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Chen, Zhan-Guo
Wei, Jun-Fa
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0
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0
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0
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Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Wei, Jun-Fa
Wang, Ming-Zhen
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0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Wang, Ming-Zhen
Zhou, Li-Yan
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Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
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Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shi, Xian-Ying
[J].
ADVANCED SYNTHESIS & CATALYSIS,
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Copper Powder-Catalyzed Regio- and Stereoselective Aminobromination of α,β-Unsaturated Ketones with TsNH2 and NBS as Nitrogen and Halogen Sources
Chen, Zhan-Guo
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0
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0
h-index:
0
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Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Chen, Zhan-Guo
Wei, Jun-Fa
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0
h-index:
0
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Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Wei, Jun-Fa
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Peking Univ, Sch Pharmaceut Sci, Beijing 100083, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Li, Run-Tao
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Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shi, Xian-Ying
Zhao, Peng-Fei
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h-index:
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Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
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JOURNAL OF ORGANIC CHEMISTRY,
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On the Absolute Configurational Stability of Bromonium and Chloronium Ions
Denmark, Scott E.
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0
引用数:
0
h-index:
0
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Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Denmark, Scott E.
Burk, Matthew T.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Burk, Matthew T.
Hoover, Andrew J.
论文数:
0
引用数:
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h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Hoover, Andrew J.
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2010,
132
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Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation
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Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
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Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Shi, Yian
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2008,
130
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4
→
共 33 条
[1]
Amatore M., 2009, Angew. Chem, V121, P5223
[2]
Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation
Amatore, Muriel
论文数:
0
引用数:
0
h-index:
0
机构:
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Amatore, Muriel
Beeson, Teresa D.
论文数:
0
引用数:
0
h-index:
0
机构:
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Beeson, Teresa D.
Brown, Sean P.
论文数:
0
引用数:
0
h-index:
0
机构:
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Brown, Sean P.
MacMillan, David W. C.
论文数:
0
引用数:
0
h-index:
0
机构:
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
MacMillan, David W. C.
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2009,
48
(28)
: 5121
-
5124
[3]
[Anonymous], ANGEW CHEM
[4]
Investigation of the early steps in electrophilic bromination through the study of the reaction with sterically encumbered olefins
Brown, RS
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Queen's University, Kingston
Brown, RS
[J].
ACCOUNTS OF CHEMICAL RESEARCH,
1997,
30
(03)
: 131
-
137
[5]
Cardona F, 2009, NAT CHEM, V1, P269, DOI [10.1038/nchem.256, 10.1038/NCHEM.256]
[6]
Aluminium Powder-Catalyzed Regio- and Stereoselective Aminobromination of α,β-Unsaturated Carbonyl Compounds and Simple Olefins with the p-Toluenesulfonamide/N-Bromosuccinimide (TsNH2-NBS) System
Chen, Zhan-Guo
论文数:
0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Chen, Zhan-Guo
Wei, Jun-Fa
论文数:
0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Wei, Jun-Fa
Wang, Ming-Zhen
论文数:
0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Wang, Ming-Zhen
Zhou, Li-Yan
论文数:
0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Zhou, Li-Yan
Zhang, Cong-Jie
论文数:
0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Zhang, Cong-Jie
Shi, Xian-Ying
论文数:
0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shi, Xian-Ying
[J].
ADVANCED SYNTHESIS & CATALYSIS,
2009,
351
(14-15)
: 2358
-
2368
[7]
Copper Powder-Catalyzed Regio- and Stereoselective Aminobromination of α,β-Unsaturated Ketones with TsNH2 and NBS as Nitrogen and Halogen Sources
Chen, Zhan-Guo
论文数:
0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Chen, Zhan-Guo
Wei, Jun-Fa
论文数:
0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Wei, Jun-Fa
Li, Run-Tao
论文数:
0
引用数:
0
h-index:
0
机构:
Peking Univ, Sch Pharmaceut Sci, Beijing 100083, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Li, Run-Tao
Shi, Xian-Ying
论文数:
0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shi, Xian-Ying
Zhao, Peng-Fei
论文数:
0
引用数:
0
h-index:
0
机构:
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China
Zhao, Peng-Fei
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2009,
74
(03)
: 1371
-
1373
[8]
De Kimpe N., 1990, CHEM ALPHA HALOKETON
[9]
On the Absolute Configurational Stability of Bromonium and Chloronium Ions
Denmark, Scott E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Denmark, Scott E.
Burk, Matthew T.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Burk, Matthew T.
Hoover, Andrew J.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Hoover, Andrew J.
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2010,
132
(04)
: 1232
-
+
[10]
Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation
Du, Haifeng
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Du, Haifeng
Zhao, Baoguo
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Zhao, Baoguo
Shi, Yian
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Shi, Yian
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2008,
130
(27)
: 8590
-
+
←
1
2
3
4
→