Optical resolution of (+/-)-1,2-Bis(2-methylphenyl)ethylene-1,2-diamine as a chiral framework for 2-iminoimidazolidine with 2-methylphenyl pendant and the guanidine-catalyzed asymmetric michael reaction of tert-butyl diphenyliminoacetate and ethyl acrylate

J Org Chem. 2008 Jan 4;73(1):133-41. doi: 10.1021/jo701923z. Epub 2007 Dec 7.

Abstract

(+/-)-1,2-Bis(2-methylphenyl)ethylene-1,2-diamine, prepared from benzil and ammonium acetate, was optically resolved as a chiral framework for 2-(1-benzyl-2-hydroxyethyl)imino-1,3-dimethylimidazolidine with 2-methylphenyl pendants at the 4,5-positions. Catalysis ability of the 1,3-dimethyl-4,5-bis(2-methylphenyl)imidazolidine and the related 1,3-dibenzyl-4,5-diphenylimidazolidine was examined in the asymmetric Michael reaction of t-butyl diphenyliminoacetate and ethyl acrylate.

MeSH terms

  • Acetates / chemistry*
  • Acrylates / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Ethylenediamines / chemical synthesis*
  • Ethylenediamines / chemistry
  • Guanidine / chemistry*
  • Imidazolidines / chemistry*
  • Imines / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism

Substances

  • 1,2-bis(2-methylphenyl)ethylene-1,2-diamine
  • 2-(1-benzyl-2-hydroxyethyl)imino-1,3-dimethylimidazolidine
  • Acetates
  • Acrylates
  • Ethylenediamines
  • Imidazolidines
  • Imines
  • tert-butyl diphenyliminoacetate
  • ethyl acrylate
  • Guanidine