An Atom-Economic Synthesis of Bicyclo[3.1.0]hexanes by Rhodium N-Heterocyclic Carbene-Catalyzed Diastereoselective Tandem Hetero-[5+2] Cycloaddition/Claisen Rearrangement Reaction of Vinylic Oxiranes with Alkynes

被引：81

作者：

Feng, Jian-Jun ^{[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 | 2011年 / 133卷 / 19期

关键词：

INTRAMOLECULAR 5+2 CYCLOADDITIONS; 2+2+2 CARBOCYCLIZATION REACTIONS; UNSATURATED TERMINAL EPOXIDES; PAUSON-KHAND REACTION; ONE-POT SYNTHESIS; GAMMA-BUTYROLACTONES; 7-MEMBERED RINGS; CYCLOISOMERIZATION REACTIONS; 1,3-DIPOLAR CYCLOADDITION; CYCLOPROPANATION REACTION;

D O I：

10.1021/ja2014604

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first synthetic application of a vinylic oxirane as a heteroatom-containing five-atom component in transition-metal-catalyzed cycloaddition reactions is reported. A new, efficient, diastereoselective tandem intramolecular hetero-[5 + 2] cycloaddition/Claisen rearrangement of vinylic oxirane-alkyne substrates that uses a rhodium NHC complex and provides strategically novel, atom-economic, regiospecific, and diastereoselective access to [3.1.0] bicyclic products has been developed.

引用

收藏

页码：7304 / 7307

页数：4

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