311310-15-3Relevant academic research and scientific papers
Resolution of pentafluorophenyl 2-phenylpropanoate using combinations of quasi-enantiomeric oxazolidin-2-ones
Shaye, Najla Al,Benoit, David M.,Chavda, Sameer,Coulbeck, Elliot,Dingjan, Marco,Eames, Jason,Yohannes, Yonas
, p. 413 - 438 (2011/06/17)
The kinetic, mutual and parallel resolution of a series of structurally related active esters derived from 2-phenylpropanoic acid using a combination of quasi-enantiomeric oxazolidin-2-ones is discussed.
Efficient parallel resolution of pentafluorophenyl active esters using quasi-enantiomeric combinations of oxazolidin-2-ones
Shaye, Najla Al,Chavda, Sameer,Coulbeck, Elliot,Eames, Jason,Yohannes, Yonas
experimental part, p. 439 - 463 (2011/06/17)
The parallel resolution of racemic pentafluorophenyl 2-aryl/ phenylpropanoates and butanoates using an equimolar combination of quasi-enantiomeric Evans oxazolidin-2-ones is discussed. The levels of diastereoselectivity were excellent (>90% de) leading to separable quasi-enantiomeric oxazolidin-2-ones in good yield. This methodology was used to resolve a series of structurally related 2-aryl/phenylpropanoic and butanoic acids.
Resolution of pentafluorophenyl esters using oxazolidin-2-ones
Al Shaye, Najla,Eames, Jason
scheme or table, p. 5892 - 5895 (2010/11/18)
A series of structurally related racemic pentafluorophenyl active esters were resolved using an equimolar amount of (S)-4-phenyloxazolidin-2-one. The levels of diastereocontrol were found to be excellent (80-96% de) at ～40% conversion.
SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one
Bull, Steven D.,Davies, Stephen G.,Garner, A. Christopher,Kruchinin, Dennis,Key, Min-Suk,Roberts, Paul M.,Savory, Edward D.,Smith, Andrew D.,Thomson, James E.
, p. 2945 - 2964 (2008/02/09)
The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions. The Royal Society of Chemistry 2006.
Investigations into the parallel kinetic resolution of 2-phenylpropanoyl chloride using quasi-enantiomeric oxazolidinones
Chavda, Sameer,Coulbeck, Elliot,Coumbarides, Gregory S.,Dingjan, Marco,Eames, Jason,Ghilagaber, Stephanos,Yohannes, Yonas
, p. 3386 - 3399 (2007/10/03)
The resolution of 2-phenylpropanoyl chloride using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were found to be dependent upon the structural nature of the metallated oxazolidinone, temperature and metal counter-ion.
Probing the resolution of 2-phenylpropanoyl chloride using quasi-enantiomeric Evans' oxazolidinones
Coumbarides, Gregory S.,Eames, Jason,Flinn, Anthony,Northen, Julian,Yohannes, Yonas
, p. 849 - 853 (2007/10/03)
The parallel kinetic resolution of 2-phenylpropanoyl chloride using quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were found to be dependent on the presence of an additional (quasi)-enantiomeric oxazolidinone and its s
Copper(II)-catalyzed kinetic resolution of (±)-2-arylpropionic acids with chiral N-trimethylsilyloxazolidin-2-one
Fukuzawa, Shin-Ichi,Chino, Yoshiaki,Yokoyama, Tetsuhiro
, p. 1645 - 1649 (2007/10/03)
The reaction between (±)-2-arylpropanoyl chlorides 1 (2 equiv.) and enantiopure N-trimethylsilyloxazolidin-2-one 2 in the presence of a catalytic amount of CuCl2 in hexane affords the corresponding N-acyloxazolidin-2-one in good chemical yields (97%) with up to 50% de.
