Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone: A new ambident diene

被引:56
作者
Cho, CG [1 ]
Kim, YW
Lim, YK
Park, JS
Lee, H
Koo, S
机构
[1] Hanyang Univ, Dept Chem, Seoul 131791, South Korea
[2] Hanyang Univ, Dept Chem Engn, Seoul 131791, South Korea
关键词
D O I
10.1021/jo015804r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
D-A cycloadditions of 3,5-dibromo-2-pyrone were investigated with a series of electronically and sterically distinct dienophiles. Our results showed that it is a highly potent ambident diene, being more reactive and stereoselective than monobromo-2-pyrones, and thus capable of generating a variety of bicycloadducts in much higher chemical yields and endo/exo ratios than monobromo-2-pyrones. Another interesting feature of this study is that the two bromine groups on the cycloadducts could be independently manipulated to produce other synthetically useful bicyclolactones.
引用
收藏
页码:290 / 293
页数:4
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