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Gold-Catalyzed Tandem Reactions of Methylenecyclopropanes and Vinylidenecyclopropanes
Alternative Title金催化的亚甲基和亚乙烯基环丙烷的串联反应研究
Zhang DH(章迪翰); Tang XY(唐翔鹰); Shi M(施敏)
Source PublicationAccounts Chem. Res.
AbstractGold catalysis is often the key step in the synthesis of natural products, and Is a powerful tool for tandem or domino reaction processes. Both gold salts and complexes are among the most powerful soft Lewis adds for electrophilic activation of carbon carbon multiple bonds toward a variety of nucleophiles. The core of these reactions relies on the interaction between gold catalysts and pi-bonds of alkenes, alkynes, and allenes. Activation of functional groups by gold complexes provides a useful and important method for facilitating many different organic transformations with high atom efficiency. Although they are highly strained, methylenecyclopropanes (MCPs) and vinylidenecyclopropanes (VDCPs) are readily accessible molecules that have served as useful building blocks in organic synthesis. Because of their unique structural and electronic properties, significant developments have been made in the presence of transition metal catalysts such as nickel, rhodium, palladium, and ruthenium during the past decades. However, less attention has been paid to the gold-catalyzed chemistry of MCPs and VDCPs. In this Account, we describe gold-catalyzed chemical transformations of MCPs and VDCPs developed both in our laboratory and by other researchers. Chemists have demonstrated that MCPs and VDCPs have amphiphilic properties. When MCPs or VDCPs are activated by a gold catalyst, subsequent nucleophillic attack by other reagents or ring-opening (ring-expansion) of the cyclopropane moiety will occur. However, the C-C double bonds of MCPS and VDCPs can also serve as nucleophilic reagents while more electrophilic reagents are present and activated by gold catalyst, and then further cascade reactions take place as triggered by the release of ring strain of cyclopropane. Based on this strategy, both our group and others have found some Interesting gold-catalyzed transformations in recent years. These transformations of MCPs and VDCPs can produce a variety of polycyclic and heterocyclic structures, containing different sized skeletons. Moreover, we have carried out some Isotopic labeling experiments and computational studies for mechanistic investigation. These reactions always give the desired products with high level control of chemo-, reglo-, and diastereoselectivities, making them highly valuable for the synthesis of natural products and to the pharmaceutical industry and medicine in general.
Subject Area金属有机化学
Indexed BySCI
Citation statistics
Cited Times:174[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Corresponding AuthorTang XY(唐翔鹰); Shi M(施敏)
Recommended Citation
GB/T 7714
Zhang DH,Tang XY,Shi M. Gold-Catalyzed Tandem Reactions of Methylenecyclopropanes and Vinylidenecyclopropanes[J]. Accounts Chem. Res.,2014,47(3):913-924.
APA 章迪翰,唐翔鹰,&施敏.(2014).Gold-Catalyzed Tandem Reactions of Methylenecyclopropanes and Vinylidenecyclopropanes.Accounts Chem. Res.,47(3),913-924.
MLA 章迪翰,et al."Gold-Catalyzed Tandem Reactions of Methylenecyclopropanes and Vinylidenecyclopropanes".Accounts Chem. Res. 47.3(2014):913-924.
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