65817-65-4Relevant academic research and scientific papers
Organocatalytic Asymmetric Cascade Aerobic Oxidation and Semipinacol Rearrangement Reaction: A Visible Light-Induced Approach to Access Chiral 2,2-Disubstituted Indolin-3-ones
Bu, Liwei,Li, Jiangtao,Yin, Yanli,Qiao, Baokun,Chai, Guobi,Zhao, Xiaowei,Jiang, Zhiyong
, p. 2382 - 2387 (2018)
An enantioselective cascade aerobic oxidation and semipinacol rearrangement reaction of 2-aryl-3-alkyl-substituted indoles via visible-light-driven cooperative organophotoredox and H-bonding catalysis is reported. The current method provides an expedient and sustainable approach to furnish a variety of valuable chiral 2-aryl-2-alkyl-substituted indolin-3-ones in 64–90 % yield with 58–94 % ee. Preliminary control experiments present important insights into the stereochemistry.
Photocatalytic aerobic oxidation/semipinacol rearrangement sequence: A concise route to the core of pseudoindoxyl alkaloids
Ding, Wei,Zhou, Quan-Quan,Xuan, Jun,Li, Tian-Ren,Lu, Liang-Qiu,Xiao, Wen-Jing
supporting information, p. 4648 - 4652 (2014/12/10)
A visible light-induced photocatalytic aerobic oxidation/semipinacol rearrangement has been successfully developed. This methodology allows for efficient conversion of a wide range of indoles into the synthetically significant 2,2-disubstituted indolin-3-ones, the core structure of pseudoindoxyl alkaloids, under mild reaction conditions.
Tandem organocatalysis and photocatalysis: An anthraquinone-catalyzed indole-c3-alkylation/photooxidation/1,2-shift sequence
Lerch, Stephanie,Unkel, Lisa-Natascha,Brasholz, Malte
supporting information, p. 6558 - 6562 (2014/06/24)
Quinones exhibit orthogonal ground- and excited-state reactivities and are therefore highly suitable organocatalysts for the development of sequential catalytic processes. Herein, the discovery of an anthraquinone-catalyzed thermal indole-C3-alkylation with benzylamines is described, which can be combined sequentially with a new visible-light-driven catalytic photooxidation/1,2-shift reaction. The one-flask tandem process converts indoles into 3-benzylindole intermediates, which are further transformed into new fluorescent 2,2-disubstituted indoline-3-one derivatives.
Reaction of arynes with amino acid esters
Okuma, Kentaro,Matsunaga, Nahoko,Nagahora, Noriyoshi,Shioji, Kosei,Yokomori, Yoshinobu
supporting information; experimental part, p. 5822 - 5824 (2011/06/23)
An efficient route to a variety of 2-phenylindolin-3-ones from amino acid methyl esters has been developed. The reaction of amino acid methyl esters with benzyne prepared from 2-(trimethylsilyl)phenyl triflate and CsF gave 2-phenylindolin-3-ones in moderate to good yields.
Study of the addition of Grignard reagents to 2-aryl-3H-indol-3-ones
Liu, Yahua,McWhorter Jr., William W.
, p. 2618 - 2622 (2007/10/03)
Grignard reagents are added to the carbonyl group of 2-aryl-3H-indol-3-ones to generate 3-alkyl-(or phenyl)-2-aryl-3H-indol-3-ols, which are in turn rearranged to yield 2-alkyl(or phenyl)-2-aryl-1,2-dihydro-3H-indol-3-ones.
