Synthesis of Enaminones by Rhodium-Catalyzed Denitrogenative Rearrangement of 1-(N-Sulfonyl-1,2,3-triazol-4-yl)alkanols

被引：155
作者：
Miura, Tomoya [1 ]
Funakoshi, Yuuta [1 ]
Morimoto, Masao [1 ]
Biyajima, Tsuneaki [1 ]
Murakami, Masahiro [1 ]
机构：
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 42期
关键词：
ONE-POT SYNTHESIS; RING-EXPANSION; REGIOSELECTIVE SYNTHESIS; TRANSANNULATION; KETONES; 2-DIMETHYLAMINOMETHYLENE-1,3-DIONES; DINUCLEOPHILES; DERIVATIVES; REACTIVITY; MIGRATION;
D O I：
10.1021/ja308285r
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Enaminones are synthesized by the rhodium(II)-catalyzed denitrogenative rearrangement reaction of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols, which are readily prepared from propargylic alcohols and N-sulfonyl azides. Intramolecular 1,2-hydride (or -alkyl) migration occurs with an intermediary alpha-imino rhodium-(II) carbenoid species generated through denitrogenation of the 1,2,3-triazol-4-yl moiety. The resulting enaminones is converted into various heterocycles with replacement of the N-sulfonyl group.
引用
收藏
页码：17440 / 17443
页数：4
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