Lewis-Acid-Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]-Cycloaddition of Epoxides with Donor-Acceptor Cyclopropanes: Synthesis of Functionalized Tetrahydrofurans

被引：46

作者：

Pandey, Ashok Kumar ^{[1
]}

Ghosh, Asit ^{[1
]}

Banerjee, Prabal ^{[1
]}

机构：

[1] Indian Inst Technol Ropar, Dept Chem, Rupnagar 140001, Punjab, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 11期

关键词：

Asymmetric synthesis; Cyclization; Oxygen heterocycles; Small ring systems; Epoxides; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; 3+2 CYCLOADDITION; ALDEHYDES; ANNULATIONS; NITRONES; REARRANGEMENT; CONSTRUCTION; ROUTES;

D O I：

10.1002/ejoc.201403590

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Lewis-acid-catalysed tandem Meinwald rearrangement/[3+2]-cycloaddition of epoxides with donor-acceptor cyclopropanes to synthesize varieties of cis-2,5-aryl-benzyl-substituted tetrahydrofurans is described. An enantioselective version of the same transformation was achieved using an InCl3-PyBOX catalyst system.

引用

页码：2517 / 2523

页数：7

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