878549-72-5Relevant academic research and scientific papers
Gold-Catalyzed Cycloisomerization–Halogenation Sequence of 1,3-Enyne Esters with NXS: Efficient Synthesis of 5-Bromo/Iodo Cyclopentenones
Zhou, Yuanyuan,Chen, Xianxiao,Yin, Dongliang,Ling, Yuan,Wang, Shifa,Zhang, Xiaoxiang,Rao, Weidong
, p. 999 - 1007 (2019)
An efficient synthetic approach for the synthesis of 5-bromo/iodo-cyclopentenones containing a C–X (Br, I) stereocenter that relies on gold(I)-catalyzed cycloisomerization–electrophilic halogenation sequence of 1,3-enyne esters with N-bromosuccinimide (NB
Development of a [2 + 2]-Nitroso/Alkene Cycloaddition Using Sodium Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate Catalyst: Controlled Chemoselectivity of Two Equilibrating Isomeric Intermediates
Chen, Jia-Xuan,Jadhav, Prakash D.,Chen, Ching-Nung,Liu, Rai-Shung
, p. 6246 - 6251 (2021/08/30)
Sodium tetrakis[3,5-bis(trifluoromethyl)-phenyl]borate (NaBArF) catalyzes the [2 + 2] cycloaddition of 1,4-disubstituted cyclopenta-1,3-dien-2-yl esters with nitrsobenzene in toluene, affording two isolable regioisomers of 6-oxa-7-azabicyclo[3.2.0] heptanes, which thermally rearrange into the same 4-aminocyclopent-1-en-3-ones. In the case of 4-substituted cyclopenta-1,3-dien-2-yl esters, their initial [2 + 2] cycloaddition intermediates undergo a rapid ring expansion to afford six-membered piperidone derivatives efficiently.
Gold(I)-Catalyzed Tandem Cycloisomerization and Fluorination of 1,3(4)-Enyne Esters with NFSI: One-Pot Assembly of 5-Fluoro- Cyclopentenones
Chen, Xianxiao,Zhou, Yuanyuan,Hong, Mei,Ling, Yuan,Yin, Dongliang,Wang, Shifa,Zhang, Xiaoxiang,Rao, Weidong
, p. 3700 - 3708 (2018/09/12)
An efficient synthetic approach for the synthesis of 5-fluoro-cyclopentenones containing a fluorine-substituted carbon stereocenter that relies on gold(I)-catalyzed cycloisomerization and fluorination sequence of 1,3(4)-enyne esters with N-fluorbenzensulfonimide (NFSI) is described. This tandem transformation exhibited a broad substrate scope and excellent functional group compatibility, providing a novel protocol for rapid assembly 5-fluoro-cyclopentenones in good to excellent yields under mild reaction conditions. The mechanistic studies revealed that the transformation involves a gold-catalyzed cycloisomerization and electrophilic fluorination cascade to give the 5-fluoro-cyclopentenones. (Figure presented.).
Efficient synthesis of cyclopentenones from enynyl acetates via tandem Au(I)-catalyzed 3,3-rearrangement and the Nazarov reaction
Zhang, Liming,Wang, Shaozhong
, p. 1442 - 1443 (2007/10/03)
A highly efficient method for the synthesis of versatile cyclopentenones from readily available enynyl acetates via tandem Au(I)-catalyzed 3,3-rearrangement and the Nazarov reaction is developed. Significant substrate flexibility and excellent control of the double bond position in the cyclopentenone ring render this an attractive method for cyclopentenone synthesis. Copyright
