Catalytic Asymmetric Bromoamination of Chalcones: Highly Efficient Synthesis of Chiral α-Bromo-β-Amino Ketone Derivatives

被引:159
作者
Cai, Yunfei [1 ]
Liu, Xiaohua [1 ]
Hui, Yonghai [1 ]
Jiang, Jun [1 ]
Wang, Wentao [1 ]
Chen, Weiliang [1 ]
Lin, Lili [1 ]
Feng, Xiaoming [1 ]
机构
[1] Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
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
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