60512-44-9Relevant academic research and scientific papers
Gold(I)-Catalyzed Ring Expansion of Alkynylcyclopropyl Allyl Ethers to Construct Tetrasubstituted Methylenecyclobutanones: A Mechanistic Investigation about the Character of Catalytic Amount of Water
Zang, Wenqing,Wang, Lei,Wei, Yin,Shi, Min,Guo, Yinlong
supporting information, p. 2321 - 2328 (2019/04/13)
A gold(I)-catalyzed ring expansion of alkynylcyclopropyl allyl ethers to produce tetrasubstituted methylenecyclobutanones in moderate to good yields has been disclosed in this paper. This reaction proceeded through an intramolecular [3,3]-sigmatropic rearrangement followed by [1,2]-allyl shift pathway in the presence of catalytic amount of water upon gold(I) catalysis. The intriguing reaction mechanism has been proposed on the basis of deuterium and 18O-labeling experiments, Mass spectroscopic analysis, 1H and 13C nuclear magnetic resonance (NMR) spectroscopic tracking and density functional theory (DFT) calculations. The further transformation of these methylenecyclobutanones into polycyclic skeleton has been realized by a practical three-step synthetic procedure. Several other transformations have been also indicated. (Figure presented.).
A convenient new method to construct 1-alkynyl cyclopropanol and its synthetic application to prepare trisubstituted dienones
An, Yan,Liu, Jie,Jiang, Hai-Ying,Wang, Yahui,Chen, Zili
, p. 3124 - 3128 (2008/09/20)
A new synthetic route was developed via the nucleophilic addition of lithium alkynylide to 1-arylsulfonyl cyclopropanol 1 to afford 1-alkynyl cyclopropanol, which then reacted with aryl iodide to construct trisubstituted cross-conjugated dienones through
Unprecedented consecutive, competitive nucleophilic addition to construct densely functionalized propargylic alcohols
Liu, Jie,An, Yan,Wang, Ya-Hui,Jiang, Hai-Ying,Zhang, Yu-Xin,Chen, Zili
supporting information; experimental part, p. 9131 - 9134 (2009/09/06)
An efficient one-pot process to construct a series of polyfunctionalized propargylic alcohol derivatives from the simple materials without functional protection was investigated. A solution of nBuLi in hexane was added into dry THF by syringe the resulting solution was then maintained at RT for 3 hours. the freshly prepared lithium enolate of acetaldehyde was used directly in the reaction. The nBuLi was added over a period of 30 minutes by syringe to a solution of terminal alkyne in THF at -30°C. The scope and limitations of the reaction was explored by examining other terminal alkynes. A number of different carbonyl-containing substrates were also examined. It was observed that propargylic alcohol derivatives are important synthetic intermediates in organic synthesis.
