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The reaction of aromatic dialdehydes with enantiopure 1,2-diamines: an expeditious route to enantiopure tricyclic amidines

Authors :
Joanna M. Redmond
Rebecca H. Pouwer
Thais Cailleau
Andrew J. P. White
Gemma Cansell
Stephen A. Hermitage
D. Christopher Braddock
Source :
Tetrahedron: Asymmetry. 21:2911-2919
Publication Year :
2010
Publisher :
Elsevier BV, 2010.

Abstract

The condensation of enantiopure 1,2-diamines with terephthalaldehyde, isophthalaldehyde or 2-iodo-, 2-alkyl- or 2-aryl-1,3-benzenedialdehydes in toluene followed by treatment with NBS in dichloromethane gives direct access to enantiopure 1,4-, and 1,3-di(4,5-dihydro-1H-imidazol-2-yl)benzenes (diamidines). The condensation of o-phthalaldehyde, and other ortho-disubstituted aromatic dialdehydes, with enantiopure 1,2-diamines, without NBS, gives enantiopure 3,5-dihydro-2H-imidazol-[2,1]-isoindoles.

Details

ISSN :
09574166
Volume :
21
Database :
OpenAIRE
Journal :
Tetrahedron: Asymmetry
Accession number :
edsair.doi...........ad61afd462e02dff0c7df16956758a7f
Full Text :
https://doi.org/10.1016/j.tetasy.2010.12.002