A one-pot synthesis of 3-arylglutaric anhydrides by reaction of ketene with aromatic aldehydes and ketones

被引:5
|
作者
Matsunaga, Hirokazu [1 ]
Ikeda, Kiyoshi [1 ]
Iwamoto, Ken-ichi [1 ]
Suzuki, Yumiko [1 ]
Sato, Masayuki [1 ]
机构
[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan
关键词
DESYMMETRIZATION;
D O I
10.1016/j.tetlet.2009.02.193
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aromatic aldehydes and ketones react with ketene under Lewis acid catalysis to produce beta-lactones, which in situ react with another molecule of ketene to produce 3-arylglutaric anhydrides. The mechanism, scope, and limitation of this one-pot synthesis of 3-substituted glutaric anhydrides are discussed. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2334 / 2336
页数:3
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