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

被引：31
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
收藏
页码：729 / 735
页数：7
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