Stereoselective synthesis of quaternary center bearing azetines and their beta-amino acid derivatives.

@article{MacNevin2008StereoselectiveSO,
  title={Stereoselective synthesis of quaternary center bearing azetines and their beta-amino acid derivatives.},
  author={Christopher J. MacNevin and Rhonda L. Moore and Dennis C Liotta},
  journal={The Journal of organic chemistry},
  year={2008},
  volume={73 4},
  pages={
          1264-9
        }
}
We describe here the use of a stable, four-membered azetine heterocycle for the preparation of highly substituted beta-amino acid derivatives. Imidazolidinone chiral auxiliaries were found to eliminate a competitive reaction pathway that had been present under previously reported conditions for azetine synthesis. The ephedrine derived imidazolidin-2-one 21 was allowed to react as its chlorotitanium enolate with O-methyl or -benzyl oximes under optimized conditions to gain improved access to… CONTINUE READING