Gold-catalyzed cyclization of allene-substituted malonate esters:: Synthesis of β,γ-unsaturated δ-lactones

被引：38

作者：

Piera, Julio ^{[1
]}

Krumlinde, Patrik ^{[1
]}

Strubing, Dirk ^{[1
]}

Backvall, Jan-E ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 11期

关键词：

D O I：

10.1021/ol070793v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the preparation of beta,gamma-unsaturated delta-lactones has been developed. The starting materials for the synthesis of these compounds are allene-substituted malonates which undergo gold-catalyzed cyclization by means of nucleophilic attack of the ester moiety on the allene. It is worth mentioning that this is the first example where an ester group attacks as a nucleophile in a gold-catalyzed transformation of allenes.

引用

页码：2235 / 2237

页数：3

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[1] Nucleophilic transition metal based cyclization of allenes [J].

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[4] PtCl2-catalyzed cycloisomerizations of allenynes [J].

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Aubert, C ;

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Marco-Contelles, J .

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[5] Saturated and unsaturated lactones [J].

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