Solid-phase synthesis of β-keto esters via sequential Baylis-Hillman and Heck reactions

被引：43
|
作者：
Kulkarni, BA [1 ]
Ganesan, A [1 ]
机构：
[1] Natl Univ Singapore, Inst Mol & Cell Biol, Singapore 117609, Singapore
来源：
JOURNAL OF COMBINATORIAL CHEMISTRY | 1999年 / 1卷 / 05期
关键词：
D O I：
10.1021/cc990007g
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Acrylic acid was immobilized on polystyrene-Wang resin, followed by Baylis-Hillman reaction with aldehydes using DABCO as catalyst. Addition of 1 equiv of lanthanum(III) trifluoromethanesulfonate was found to improve yields, as in solution phase. After the Baylis-Hillman step, Heck reaction with aryl halides resulted in alpha-substituted beta-keto esters, which were cleaved from the resin by acid hydrolysis with concomitant decarboxylation to afford aryl ketone products. Overall yields of 0-49% were obtained with 26 examples.
引用
收藏
页码：373 / 378
页数：6
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