Cycloisomerization of Acetylenic Acids to γ-Alkylidene Lactones using a Palladium(II) Catalyst Supported on Amino-Functionalized Siliceous Mesocellular Foam

被引：31

作者：

Nagendiran, Anuja ^{[1
]}

Verho, Oscar ^{[1
]}

Haller, Clemence ^{[1
]}

Johnston, Eric V. ^{[1
]}

Backvall, Jan-E. ^{[1
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 03期

基金：

瑞典研究理事会;

关键词：

ALKYNOIC ACIDS; CARBOXYLIC-ACIDS; AQUEOUS-MEDIA; CYCLIZATION; METAL; EFFICIENT; NANOPALLADIUM; NANOPARTICLES; ACCESS;

D O I：

10.1021/jo4028006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloisomerization of various gamma-acetylenic acids to their corresponding gamma-alkylidene lactones by the use of a heterogeneous Pd(II) catalyst supported on amino-functionalized siliceous mesocellular foam is described. Substrates containing terminal as well as internal alkynes were cyclized in high to excellent yields within 2-24 h under mild reaction conditions. The protocol exhibited high regio- and stereoselectivity, favoring the exo-dig product with high Z selectivity. Moreover, the catalyst displayed excellent stability under the employed reaction conditions, as demonstrated by its good recyclability and low leaching.

引用

页码：1399 / 1405

页数：7

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