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- W2059348850 abstract "The cycloisomerization reaction of N-allyl-2-(2′-arylethyne-2-yl)amides or allylic 2-alkynoates in the presence of cationic triphenylphosphinegold(I) produced bicyclo[3.2.0]hept-6-en-2-ones under mild conditions. Computational investigations with a density functional theory (DFT) revealed that a stepwise 6-endo-dig cyclization of 1,6-enyne systems, followed by a skeletal rearrangement to form bicyclo[3.2.0]hept-6-en-2-one species represents the most probable reaction pathway. This can be further supported by employing N-(1′,1′-dimethyl-1-propen-3-yl)-2-(1′′-phenylethyne-2′′-yl)amide as a substrate, which exclusively produced 4-phenyl-5-(prop-1-en-2-yl)-5,6-dihydropyridino-2(1H)-one unambiguously via 6-endo-dig cyclization. Theoretical calculations suggest both an aryl group at the terminal alkyne and a keto carbonyl at the C(5) position of the 1,6-enyne system play a complementary role for the reactivity." @default.
- W2059348850 created "2016-06-24" @default.
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- W2059348850 date "2009-09-22" @default.
- W2059348850 modified "2023-10-09" @default.
- W2059348850 title "Au(I)-Catalyzed Cycloisomerization Reaction of Amide- or Ester-Tethered 1,6-Enynes to Bicyclo[3.2.0]hept-6-en-2-ones" @default.
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- W2059348850 doi "https://doi.org/10.1021/jo901771p" @default.
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