862907-10-6Relevant articles and documents
Microfluidic Visible-Light Paternò–Büchi Reaction of Oxindole Enol Ethers
Franceschi, Pietro,Mateos, Javier,Vega-Pe?aloza, Alberto,Dell'Amico, Luca
, p. 6718 - 6722 (2020/09/11)
A novel microfluidic visible-light process for the functionalisation of oxindoles is reported. The chemistry is based on the reactivity of the corresponding enol ethers, which participate in a site-, regio- and diastereoselective [2+2] heterocycloaddition (Paternò–Büchi) process. The mild reaction conditions, the use of available ketones, together with the high generality (23 examples) and robustness (up to gram scale) make this process a useful synthetic platform for the construction of structurally strained heterocycles.
Chincona alkaloid-catalyzed enantioselective trifluoromethylthiolation of oxindoles
Yang, Tao,Shen, Qilong,Lu, Long
, p. 678 - 680 (2014/10/16)
An organocatalytic asymmetric trifluoromethylthiolation of 3-aryl or 3-alkyloxindoles employing a trifluoromethyl-substituted thioperoxide as the electrophilic trifluoromethylthiolating reagent was described. Reactions occurred in good to excellent enanti
Phosphine-catalyzed enantioselective γ-addition of 3-substituted oxindoles to 2,3-butadienoates and 2-butynoates: Use of prochiral nucleophiles
Wang, Tianli,Yao, Weijun,Zhong, Fangrui,Pang, Guo Hao,Lu, Yixin
, p. 2964 - 2968 (2014/04/03)
The first phosphine-catalyzed enantioselective γ-addition with prochiral nucleophiles and 2,3-butadienoates as the reaction partners has been developed. Both 3-alkyl- and 3-aryl-substituted oxindoles could be employed in this process, which is catalyzed by a chiral phosphine that is derived from an amino acid, thus affording oxindoles that bear an all-carbon quaternary center at the 3-position in high yields and excellent enantioselectivity. The synthetic value of these γ-addition products was demonstrated by the formal total synthesis of two natural products and by the preparation of biologically relevant molecules and structural scaffolds.