39164-92-6Relevant academic research and scientific papers
Chiral scandium(III)-catalyzed enantioselective α-arylation of N-unprotected 3-substituted oxindoles with diaryliodonium salts
Guo, Jing,Dong, Shunxi,Zhang, Yulong,Kuang, Yulong,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
, p. 10245 - 10249 (2013)
Catalytic asymmetric α-arylation of N-unprotected 3-substituted oxindoles with diaryliodonium salts has been realized by a chiral Lewis acid promoted electrophilic addition and aryl-rearrangement process. Single C3-arylated products containing a quaternary carbon center were generated in high enantioselectivity and reactivity. Copyright
Phosphoric Acid Catalyzed 1,2-Rearrangements of 3-Hydroxyindolenines to Indoxyls and 2-Oxindoles: Reagent-Controlled Regioselectivity Enabled by Dual Activation
Schendera, Eva,Lerch, Stephanie,von Drathen, Thorsten,Unkel, Lisa-Natascha,Brasholz, Malte
supporting information, p. 3134 - 3138 (2017/06/21)
A common synthetic route to indoxyl and 2-oxindole alkaloids utilizes the oxidation of indoles to 3-hydroxyindolenines, followed by acid-mediated 1,2-rearrangement. However, controlling the regioselectivity is often challenging and there is an ongoing need for new reaction conditions allowing to steer product selectivity. We report herein that phosphoric acids are ideal organocatalysts for the highly regioselective 1,2-rearrangement of 3-hydroxyindolenines to 2-oxindoles, with predictable product selectivity arising from an efficient dual activation mode.
