Conformational control in the SuperQuat chiral auxiliary 5,5-dimethyl-4-iso-propyloxazolidin-2-one induces the iso-propyl group to mimic a tert-butyl group
1H NMR nOe spectroscopic studies reveal that conformational control in the enolates of N-acyl-5,5-dimethyl-4-iso-propyloxazolidin-2-ones ensures that the stereodirecting effect of its 4-iso-propyl-5,5-dimethyl functional group affords superior levels of facial selectivity normally associated with enolates derived from N-acyl-4-tert-butylox-azolidin-2-ones.
Investigations into the parallel kinetic resolution of 2-phenylpropanoyl chloride using quasi-enantiomeric oxazolidinones
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
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