1380340-91-9Relevant academic research and scientific papers
Scope, Limitations and Mechanistic Analysis of the HyperBTM-Catalyzed Acylative Kinetic Resolution of Tertiary Heterocyclic Alcohols**
Smith, Samuel M.,Greenhalgh, Mark D.,Feoktistova, Taisiia,Walden, Daniel M.,Taylor, James E.,Cordes, David B.,Slawin, Alexandra M. Z.,Cheong, Paul Ha-Yeon,Smith, Andrew D.
, (2021/11/16)
The full scope and limitations of the catalytic acylative kinetic resolution of a range of tertiary heterocyclic alcohols (78 examples, s up to >200) is reported under operationally-simple conditions, using low loadings of a commercially available Lewis basic isothiourea catalyst, HyperBTM (generally 1 mol %). The protocol is highly effective for the kinetic resolution of 3-substituted 3-hydroxyoxindole and α-substituted α-hydroxylactam derivatives bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. The full power of this methodology has been showcased through the synthesis of highly enantioenriched biologically-active target compounds in both enantiomeric forms. To provide further insight into the reaction mechanism, a detailed kinetic analysis of this Lewis base-catalyzed acylation of tertiary alcohols is reported using the variable time normalization analysis (VTNA) method.
Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions
Guang, Jie,Guo, Qunsheng,Zhao, John Cong-Gui
supporting information; experimental part, p. 3174 - 3177 (2012/08/28)
Highly enantioselective aldol reactions of acetylphosphonates and activated carbonyl compounds was realized with cinchona alkaloid derived catalysts, in which the acetylphosphonate was directly used as an enolate precursor for the first time. The aldol product obtained was converted in situ to its corresponding ester or amide through methanolysis or aminolysis. The overall process may be viewed as formal highly enantioselective acetate or acetamide aldol reactions, which are very difficult to achieve directly with organocatalytic methods.
