Lewis Acid-Mediated Transformations of trans-2-Aroyl-3-arylcyclopropane-1,1-dicarboxylates into 2-Pyrones and 1-Indanones

被引：32

作者：

Sathishkannan, Gopal ^{[1
]}

Srinivasan, Kannupal ^{[1
]}

机构：

[1] Bharathidasan Univ, Sch Chem, Tiruchirappalli 620024, Tamil Nadu, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 04期

关键词：

carbocycles; heterocycles; ring expansion; small ring systems; synthetic methods; DONOR-ACCEPTOR CYCLOPROPANES; NAZAROV CYCLIZATION; ALPHA-PYRONE; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; DERIVATIVES; KETONES; INDANONES; ALDEHYDES; SCOPE;

D O I：

10.1002/adsc.201300861

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

trans-2-Aroyl-3-arylcyclopropane-1,1-dicarboxylates upon treatment with aluminium(III) chloride (AlCl3) underwent ring-opening, fragmentation, recombination and lactonization to give highly substituted 2-pyrones. Alternatively, when treated with titanium(IV) chloride (TiCl4), the cyclopropane diesters underwent a Nazarov cyclization to afford 1-indanones with high diastereoselectivity.

引用

页码：729 / 735

页数：7

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