Macrolactonization via hydrocarbon oxidation

被引：195

作者：

Fraunhoffer, Kenneth J. ^{[1
]}

Prabagaran, Narayanasamy ^{[1
]}

Sirois, Lauren E. ^{[1
]}

White, M. Christina ^{[1
]}

机构：

[1] Univ Illinois, Roger Adams Lab, Dept Chem, Urbana, IL 61801 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 28期

关键词：

D O I：

10.1021/ja063096r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel Pd/sulfoxide-catalyzed macrolactonization reaction of linear ω-alkenoic acids is reported that proceeds via serial ligand-catalyzed allylic C-H oxidation. The scope of this macrolactonization appears to be very broad. Aryl, alkyl, and (Z)-α,β-unsaturated acids are all competent nucleophiles for this reaction, with the latter undergoing macrolactonization with no olefin isomerization. High functional group compatibility is observed that includes biologically and medicinally relevant functionality such as ortho-substituted salicylate esters, bis(indoyl)maleimides, and peptides. Evidence is provided to support the hypothesis that macrolactonization proceeds via inner-sphere functionalization from a templated π-allylPd carboxylate intermediate. Copyright © 2006 American Chemical Society.

引用

页码：9032 / 9033

页数：2

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