1440934-25-7Relevant 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.
supporting information, (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.
Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones
Wang, Rong-Hui,Li, Ya-Ling,He, Hong-Jiao,Xiao, You-Cai,Chen, Fen-Er
, p. 4302 - 4306 (2021/02/16)
The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.
Kinetic resolution of tertiary alcohols: Highly enantioselective access to 3-hydroxy-3-substituted oxindoles
Lu, Shenci,Poh, Si Bei,Siau, Woon-Yew,Zhao, Yu
, p. 1731 - 1734 (2013/04/10)
Enantioselective: The first highly enantioselective kinetic resolution of 3-hydroxy-3-substituted oxindoles has been developed through oxidative esterification catalyzed by a N-heterocyclic carbene (see picture). This method uses a simple procedure and provides 3-hydroxy-oxindoles with various substituents at the 3-position in excellent enantiopurity. S=selectivity. Copyright
