Asymmetric synthesis of anti-(2S,3S)- and syn-(2R,3S)-diaminobutanoic acid.

Abstract

Conjugate addition of homochiral lithium N-benzyl-N-alpha-methylbenzylamide to tert-butyl (E)-cinnamate or tert-butyl (E)-crotonate and in situ amination with trisyl azide results in the exclusive formation of the corresponding 2-diazo-3-amino esters in > 95% de. Amination of the lithium (E)-enolates of tert-butyl (3S,alphaR)-3-N-benzyl-N-alpha… (More)

Topics

Cite this paper

@article{Bunnage2003AsymmetricSO, title={Asymmetric synthesis of anti-(2S,3S)- and syn-(2R,3S)-diaminobutanoic acid.}, author={Mark E. Bunnage and Anthony J. Burke and Stephen G Davies and Nicholas L Millican and Rebecca L Nicholson and Paul M. Roberts and Andrew D. Smith}, journal={Organic & biomolecular chemistry}, year={2003}, volume={1 21}, pages={3708-15} }