Stereoselective Synthesis of 2,3-Dihydropyrroles from Terminal Alkynes, Azides, and α,β-Unsaturated Aldehydes via N-Sulfonyl-1,2,3-triazoles

被引：149

作者：

Miura, Tomoya ^{[1
]}

Tanaka, Takamasa ^{[1
]}

Hiraga, Kentaro ^{[1
]}

Stewart, Scott G. ^{[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 | 2013年 / 135卷 / 37期

关键词：

ENANTIOSELECTIVE SYNTHESIS; CATALYZED TRANSANNULATION; OLEFIN CYCLOPROPANATION; CONTROLLING SELECTIVITY; MANNICH CYCLIZATION; AZAVINYL CARBENES; DERIVATIVES; 1-SULFONYL-1,2,3-TRIAZOLES; DIHYDROPYRROLE; REARRANGEMENTS;

D O I：

10.1021/ja407166r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereoselective method for synthesis of trans-2,3-disubstituted 2,3-dihydropyrroles is reported. N-Sulfonyl-1,2,3-triazoles prepared from terminal alkynes generate a-imino rhodium carbene complexes, which when combined with alpha,beta-unsaturated aldehydes produce trans-2,3-disubstituted dihydropyrroles. The method can be successfully applied to a one-pot process starting from terminal alkynes.

引用

收藏

页码：13652 / 13655

页数：4

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