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

页码：373 / 378

页数：6

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