22618-48-0Relevant articles and documents
Enantiopure cis- and trans-2-(2-Aminocyclohexyl)phenols: Effective Preparation, Solid-State Characterization, and Application in Asymmetric Organocatalysis
Tezeren, Mustafa A.,Ye?il, Tolga A.,Zorlu, Yunus,Tilki, Tahir,Ertürk, Erkan
, p. 7017 - 7032 (2018/12/13)
Effective synthesis of cis- and trans-2-(2-methoxyphenyl)cyclohexylamine as well as their multigram-scale optical resolution by diastereomeric salt formation with dibenzoyl tartaric acid have been described. Assignment of absolute configurations to the enantiomers has been made by X-ray crystallography. Starting from the resolved precursor, diverse aminoalkylphenols (AAPs) having primary, secondary, and tertiary amine group as well as a quaternary ammonium phenol have been prepared as potential bifunctional organocatalysts based on the cyclohexane backbone. We furthermore report herein that AAPs carrying a primary amine and a phenolic hydroxyl group can catalyze the direct aldol reaction with high activity and setereoselectivity, and thus up to 97 % yield, 90:10 syn/anti diastereomeric ratio, and 80 % enantiomeric excess can be achieved.
N-heterocyclic carbene dichotomy in Pd-catalyzed acylation of aryl chlorides via C-H bond functionalization
Flores-Gaspar, Areli,Gutierrez-Bonet, Alvaro,Martin, Ruben
supporting information, p. 5234 - 5237,4 (2012/12/12)
The first Pd-catalyzed intramolecular acylation of aryl chlorides via C-H bond functionalization is presented. The method allows for the synthesis of a variety of elusive benzocyclobutenones with a wide range of functional groups and substitution patterns. We demonstrate that a change in the ligand backbone dictates the selectivity pattern.
FeCl3/Nal-catalyzed allylic C-H oxidation of arylalkenes with a catalytic amount of disulfide under air
Huang, Deshun,Wang, Haining,Xue, Fazhen,Shi, Yian
body text, p. 7269 - 7274 (2011/10/09)
This paper describes a FeCl3/NaI-catalyzed formal allylic C-H oxidation of arylalkenes using a catalytic amount of disulfide with BnOH and 4-nitroaniline as nucleophiles and air as oxidant to form the corresponding allyl ethers and amines. A possible reaction mechanism has been proposed.