Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H2NCH2CH[(CH2)(n)NHMe]NH2(n=1-4) from alpha-Amino Acids: New Agents for Asymmetric Catalysis Academic Article uri icon


  • Tris(hydrochloride) adducts of the title compounds are prepared from the inexpensive -amino acids H2N(C=O)CH2CH(NH2)CO2H, HO(C=O)(CH2) nCH(NH2)CO2H (n = 1, 2), and H2N(CH2)4CH(NH2)CO2H, respectively (steps/overall yield = 5/32%, 7/30%, 7/33%, 5/38%). The NH2 group that is remote from the secondary amine is installed via BH3 reduction of an amide [(C=O)NR2] derived from an -amino carboxylic acid. The MeNHCH2 units are introduced by BH3 reductions of alkyl carbamate [RO(C=O)NHCH2; R = Et, t-Bu] or amide [MeHN(C=O)] moieties.

published proceedings


altmetric score

  • 0.5

author list (cited authors)

  • Kabes, C. Q., Gunn, J. H., Selbst, M. A., Lucas, R. F., & Gladysz, J. A.

citation count

  • 1

complete list of authors

  • Kabes, Connor Q||Gunn, Jack H||Selbst, Maximilian A||Lucas, Reagan F||Gladysz, John A

publication date

  • November 2020