One-pot cascade synthesis of 2,3-disubstituted 2,3-dihydrobenzofurans via ortho-quinone methide intermediates generated in situ

被引：8
|
作者：
Shaikh, Abdul Kadar [1 ]
Varvounis, George [1 ]
机构：
[1] Univ Ioannina, Dept Chem, Sect Organ Chem & Biochem, GR-45110 Ioannina, Greece
来源：
RSC ADVANCES | 2015年 / 5卷 / 19期
关键词：
DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; DIHYDROBENZOFURANS; MILD;
D O I：
10.1039/c4ra15024d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A simple and efficient one-pot cascade reaction for the regioselective synthesis of trans or cis/trans 2,3-disubstituted 2,3-dihydrobenzofurans is reported. The method involves fluoride-induced desilylation, generation of o-quinone methide (o-QM) by chloride or nitrate anion elimination, Michael addition and intramolecular 5-exo-tet elimination of a bromide anion. Nitrate, acetoxy and chloride anions are compared as leaving groups in the formation of the in situ generated o-QM.
引用
收藏
页码：14892 / 14896
页数：5
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