Asymmetric synthesis of syn-(2R,3S)-and anti-(2S,3S)-ethyl diamino-3-phenylpropanoates from N-(benzylidene)-p-toluenesulfinamide and glycine enolates.
Addition of differentially N-protected glycine enolates to enantiopure sulfinimines affords syn- and anti-alpha,beta-diamino esters with high diastereoselectivities and good yields.
Department of Chemistry, Temple University, Philadelphia, PA 19122, USA. fdavis@temple.edu
Franklin A
FA
Davis
Jianghe
J
Deng
D000577:Amides / Q000737:chemistry*; D000599:Amino Acids, Diamino / Q000138:chemical synthesis; D001597:Benzylidene Compounds / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry*; D010666:Phenylpropionates / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D000599:Amino Acids, Diamino; D001597:Benzylidene Compounds; D010666:Phenylpropionates; D005998:Glycine