155341-30-3Relevant academic research and scientific papers
Amination of o-Alkenylphenols with Alkylamines via Photoinduced Proton Transfer
Yasuda, Masahide,Sone, Tatsuya,Tanabe, Kimiko,Shima, Kensuke
, p. 453 - 456 (1994)
Irradiation of o-alkenylphenols with alkylamines resulted in Markovnikov-type amination to give o-(1-alkylaminoalkyl)phenols in relatively good yields. The photoamination was initiated by a proton transfer from the ammonium ion to the alkenyl group of o-alkenylphenolate anion in the excited state in the ion pair formed between the phenols and the amines. The resulting zwitter ion allowed the nucleophilic addition of the amine at the benzylic cation center.
Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2
Hu, Le' an,Zhang, Yao,Zhang, Qing-Wen,Yin, Qin,Zhang, Xumu
supporting information, p. 5321 - 5325 (2020/02/28)
A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.
Chiral phosphoric acid-catalyzed enantioselective transfer hydrogenation of ortho-hydroxyaryl alkyl N - H ketimines
Nguyen, Thanh Binh,Bousserouel, Hadjira,Wang, Qian,Gueritte, Francoise
supporting information; body text, p. 4705 - 4707 (2010/12/24)
The first enantioselective chiral phosphoric acid-catalyzed transfer hydrogenation of unprotected ortho-hydroxyaryl alkyl N - H ketimines using Hantszch di-tert-butyl ester as a reductant is reported. A variety of ortho-hydroxybenzylamines were obtained in good to excellent yields and enantiomeric excesses.
Photochemical Reactions of o-Alkenylphenols and 1-Alkenyl-2-naphthol with Alkylamines: Amination via Photoinduced Proton Transfer
Yasuda, Masahide,Sone, Tatsuya,Tanabe, Kimiko,Shima, Kensuke
, p. 459 - 464 (2007/10/02)
Irradiation of o-alkenylphenols 1a-c and 2a-e in the presence of alkylamines gave o-(1-alkylaminoalkyl)phenols 4a-n and 5a-e in relatively good yields.Deprotonation of these o-alkenylphenols by the amines occurs in the excited singlet state to give the excited singlet state of the phenolate anion 7 and the ammonium ion.The proton transfer from the ammonium ion to the alkenyl group of 7 generates the zwitterion 8 that allows the nucleophilic addition of the amine at the benzylic cation centre.Similar photoamination of 1-(2-methylpropenyl)-2-naphthol 3 with alkylamines occured to give 1-(1-alkylamino-2-methylpropyl)-2-naphthols 6a-b.
