Transfer of Chirality in the Rhodium-Catalyzed Intramolecular Formal Hetero-[5+2] Cycloaddition of Vinyl Aziridines and Alkynes: Stereoselective Synthesis of Fused Azepine Derivatives

被引：103

作者：

Feng, Jian-Jun ^{[1
]}

Lin, Tao-Yan ^{[1
]}

Wu, Hai-Hong ^{[1
]}

Zhang, Junliang ^{[1
]}

机构：

[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 11期

关键词：

INTERMOLECULAR 5+2 CYCLOADDITION; 7-MEMBERED RINGS; REARRANGEMENT; HETEROCYCLES; REACTIVITY; 3-ACYLOXY-1,4-ENYNES; VINYLCYCLOPROPANES; ISOMERIZATION; SELECTIVITY; CYCLIZATION;

D O I：

10.1021/jacs.5b01305

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

By taking advantage of vinyl aziridines as a heteroatom-containing five-atom component in rhodium-catalyzed intramolecular formal hetero-[5 + 2] cycloaddition reactions with alkynes, a highly efficient method for the synthesis of fused azepine derivatives at 30 degrees C was developed. The reaction has broad substrate scope and tolerates a wide range of functional groups. The chirality of vinyl aziridine-alkyne substrates can be completely transferred to the cycloadducts, representing an atom-economic and enantiospecific protocol for the construction of fused 2,5-dihydroazepines for the first time.

引用

页码：3787 / 3790

页数：4

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