期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 11, 页码 3198-3204出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304579
关键词
alkynes; cycloaddition; gold; isomerization; rearrangement; vinylidenecyclopropanes
资金
- Shanghai Municipal Committee of Science and Technology [11JC1402600]
- National Basic Research Program of China (973) [2009CB825300]
- National Natural Science Foundation of China [21102166, 21072206, 20472096, 21372241, 21302203, 20672127, 21121062, 21361140350, 20732008]
A novel type of yne-vinylidenecyclopropanes (VDCPs) has been synthesized and applied in gold-catalyzed cycloisomerization reactions. It was found that these compounds can undergo an intramolecular cycloisomerization and perform as a three-carbon synthon for [3+2] cycloaddition under gold catalysis to give fused [4.3.0] and [5.3.0] bicyclic derivatives and VDCP rearranged products in moderated to good yields under mild conditions. The substrate scope of these novel transformations has been explored and plausible reaction mechanisms have been presented on the basis of deuterium labeling experiments and DFT calculations.
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