1268070-65-0Relevant academic research and scientific papers
Acylative Kinetic Resolution of Alcohols Using a Recyclable Polymer-Supported Isothiourea Catalyst in Batch and Flow
Neyyappadath, Rifahath Mon,Chisholm, Ross,Greenhalgh, Mark D.,Rodríguez-Escrich, Carles,Pericàs, Miquel A.,H?hner, Georg,Smith, Andrew D.
, p. 1067 - 1075 (2018/02/14)
A polystyrene-supported isothiourea catalyst, based on the homogeneous catalyst HyperBTM, has been prepared and used for the acylative kinetic resolution of secondary alcohols. A wide range of alcohols, including benzylic, allylic, and propargylic alcohols, cycloalkanol derivatives, and a 1,2-diol, has been resolved using either propionic or isobutyric anhydride with good to excellent selectivity factors obtained (28 examples, s values up to 600). The catalyst can be recovered and reused by a simple filtration and washing sequence, with no special precautions needed. The recyclability of the catalyst was demonstrated (15 cycles) with no significant loss in either activity or selectivity. The recyclable catalyst was also used for the sequential resolution of 10 different alcohols using different anhydrides with no cross-contamination between cycles. Finally, successful application in a continuous flow process demonstrated the first example of an immobilized Lewis base catalyst used for the kinetic resolution of alcohols in flow.
Kinetic resolution of secondary carbinols by a chiral N,N-4-dimethylaminopyridine derivative containing a 1,1′-binaphthyl unit: Hydrogen bonding affects catalytic activity and enantioselectivity
Fujii, Kazuki,Mitsudo, Koichi,Mandai, Hiroki,Suga, Seiji
, p. 1081 - 1092 (2016/10/11)
We developed an acylative kinetic resolution of secondary carbinols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1d with tert-Alcohol substituents. The reaction proceeded with a wide range of carbinols with moderate to high selectivity (s) (up to s = 79.5). Kinetic studies revealed that catalyst 1d was more catalytically active than the corresponding bis-methyl ether 1d′ or DMAP. Hydrogen bonding between tert-Alcohols of the catalyst and secondary carbinols was responsible for the enhanced reaction rate and high enantioselectivity.
A tandem asymmetric synthesis approach for the efficient preparation of enantiomerically pure 9-(hydroxyethyl) anthracene
Ball, Jennifer C.,Brennan, Paul,Elsunaki, Tareg M.,Jaunet, Alexis,Jones, Simon
scheme or table, p. 253 - 255 (2011/05/05)
A tandem approach for the preparation of gram quantities of enantiomerically pure 9-(hydroxyethyl)-anthracene is presented using an asymmetric reduction followed by kinetic resolution that has potential applicability to other chiral alcohols.
Design, synthesis, and evaluation of a helicenoidal DMAP lewis base catalyst
Crittall, Matthew R.,Rzepa, Henry S.,Carbery, David R.
supporting information; experimental part, p. 1250 - 1253 (2011/04/25)
The design, synthesis, and study of a helical dialkylaminopyridine Lewis base catalyst is reported. Helical DMAP analogue 4 is based upon a helicenoid structure and displays good to excellent levels of selectivity (S ≤ 116) in the kinetic resolution of chiral secondary alcohols. Catalyst 4 displays excellent reactivity with exceptionally low loadings of 0.05 mol % effecting practical levels of selectivity in kinetic resolutions.(Figure Presented)
