Gold-Catalyzed Oxidative Reactions of Propargylic Carbonates Involving 1,2-Carbonate Migration: Stereoselective Synthesis of Functionalized Alkenes

被引：31

作者：

Sun, Ning ^{[1
]}

Chen, Ming ^{[1
]}

Liu, Yuanhong ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 09期

基金：

中国国家自然科学基金;

关键词：

EFFICIENT SYNTHESIS; REGIOSELECTIVE OXIDATION; HIGHLY EFFICIENT; CYCLOISOMERIZATION REACTIONS; RAPID ACCESS; REARRANGEMENT; ESTERS; KETONES; DERIVATIVES; CYCLIZATION;

D O I：

10.1021/jo500573s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A gold-catalyzed oxidative reaction of propargylic carbonates or acetates using 3,5-dichloropyridine as the oxidant has been developed. The reaction provides efficient access to alpha-functionalized-alpha,beta-unsaturated ketones with excellent regio- and diastereocontrol via a regioselective attack of the N-oxide to the gold-activated alkyne followed by a 1,2-carbonate migration. In addition, the alkene products could be further transformed into the valuable 5-hydroxycyclopent-2-enones via cyclocondensation with acetone or cyclodimerization under basic conditions.

引用

页码：4055 / 4067

页数：13

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