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Gold-Catalyzed Oxidative Reactions of Propargylic Carbonates Involving 1,2-Carbonate Migration: Stereoselective Synthesis of Functionalized Alkenes
Alternative Title涉及1,2-碳酸酯迁移的炔丙基碳酸酯的金催化氧化重排反应: 多官能团化烯烃的立体选择性合成
Sun N(孙宁); Chen M(陈铭); Liu YH(刘元红)
2014
Source PublicationJ. Org. Chem.
Volume79Issue:9Pages:4055-4067
AbstractA 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.
Subject Area金属有机化学
DOI10.1021/jo500573s
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Indexed BySCI
Language英语
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Cited Times:22[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39060
Collection金属有机化学国家重点实验室
Corresponding AuthorLiu YH(刘元红)
Affiliation中科院上海有机化学研究所
Recommended Citation
GB/T 7714
Sun N,Chen M,Liu YH. Gold-Catalyzed Oxidative Reactions of Propargylic Carbonates Involving 1,2-Carbonate Migration: Stereoselective Synthesis of Functionalized Alkenes[J]. J. Org. Chem.,2014,79(9):4055-4067.
APA 孙宁,陈铭,&刘元红.(2014).Gold-Catalyzed Oxidative Reactions of Propargylic Carbonates Involving 1,2-Carbonate Migration: Stereoselective Synthesis of Functionalized Alkenes.J. Org. Chem.,79(9),4055-4067.
MLA 孙宁,et al."Gold-Catalyzed Oxidative Reactions of Propargylic Carbonates Involving 1,2-Carbonate Migration: Stereoselective Synthesis of Functionalized Alkenes".J. Org. Chem. 79.9(2014):4055-4067.
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