期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 361, 期 10, 页码 2321-2328出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900053
关键词
gold-catalyzed; alkynylcyclopropyl allyl ethers; methylenecyclobutanones; water
资金
- National Basic Research Program of China [(973)] [2015CB856603]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000, sioczz201808]
- National Natural Science Foundation of China [20472096, 21372241, 21572052, 20672127, 21421091, 21372250, 21121062, 21302203, 20732008, 21772037, 21772226, 21861132014]
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 O-18-labeling experiments, Mass spectroscopic analysis, H-1 and C-13 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.
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