Brandes, Sebastian; Bella, Marco; Kjoersgaard, Anne; Joergensen, Karl Anker published the artcile< Chirally aminated 2-naphthols-organocatalytic synthesis of non-biaryl atropisomers by asymmetric Friedel-Crafts amination>, COA of Formula: C19H34O2, the main research area is hydroxynaphthylhydrazinedicarboxamide enantioselective preparation atropisomer Friedel Crafts amination; modified cinchona alkaloid stereoselective preparation catalyst Friedel Crafts amination; enantioselective Friedel Crafts amination naphthol azodicarboxylate cinchona alkaloid catalyst; racemization barrier hydroxynaphthylhydrazinedicarboxamide; mol crystal structure bromobenzoylamino hydroxynaphthylhydrazinedicarboxamide.
Atropisomeric hydroxynaphthylhydrazinedicarboxamides I (R = H2N, MeNH, PhCH2NH, BuCH2NH; R1 = H, Br; R2 = Me3C, PhCH2), novel non-aryl atropisomers, are prepared in 85-98% yields and in 87-98% ee by amination of 2-naphthols II (R = H2N, MeNH, PhCH2NH, BuCH2NH; R1 = H, Br) with azodicarboxylates Me3CO2CN:NCO2R2 in the presence of cinchona catalysts or modified cinchona alkaloids such as III. III (prepared by addition of a dihydroquinidine-derived alkaloid to di-tert-Bu azodicarboxylate in methylene chloride under forcing conditions) and related atropisomeric hydrazine-substituted cinchona alkaloids are particularly effective catalysts for the enantioselective amination of 2-naphthols II (R = H2N, MeNH, PhCH2NH, BuCH2NH; R1 = H, Br) with di-tert-Bu azodicarboxylate; III and related compounds are configurationally stable when stored as solids at ambient temperature The barrier to racemization of di-tert-Bu (2-hydroxynaphthyl)hydrazinedicarboxylate (IV) is determined exptl. and by computational methods; atropisomers of IV are not stable at ambient temperature (t1/2 = 26 min.). I (R = 4-BrC6H4CONH; R1 = H; R2 = PhCH2) can be acylated to give amides or ureas without loss of atropisomeric purity, while cleavage of either of the carboxylate groups leads to the formation of racemic products. The structure of I (R = 4-BrC6H4CONH; R1 = H; R2 = PhCH2) is determined by X-ray crystallog.
Angewandte Chemie, International Edition published new progress about Amination catalysts (stereoselective). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, COA of Formula: C19H34O2.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics