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

被引：156

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.

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收藏

页码：17440 / 17443

页数：4

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