Catalytic carbonylation of β-lactones to succinic anhydrides

被引：50

作者：

Getzler, YDYL ^{[1
]}

Kundnani, V ^{[1
]}

Lobkovsky, EB ^{[1
]}

Coates, GW ^{[1
]}

机构：

[1] Cornell Univ, Baker Lab, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 22期

关键词：

D O I：

10.1021/ja048946m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A well-defined,highly active and selective catalyst for the synthesis of succinic anhydrides from CO and β-lactones is reported. At 200 psi of CO, the catalyst [(N,N′-bis(3,5-di-tert-butylsalicylidene)phenylenediamino)Al(THF)2][Co(CO)4] carbonylates β-propiolactones to succinic anhydrides in high yield. (R)-β-Butyrolactone is carbonylated to (S)-methylsuccinic anhydride with clean inversion of stereochemistry, while cis-2,3-dimethyl-β-propiolactone yields exclusively trans-2,3-dimethylsuccinic anhydride. These data are consistent with a mechanism involving nucleophilic attack by [Co(CO)4]- on the β carbon of the lactone, followed by CO insertion and anhydride formation. Copyright © 2004 American Chemical Society.

引用

页码：6842 / 6843

页数：2

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