Phosphoric acid catalyzed diastereo- and enantioselective synthesis of substituted 1,3-diaminotetralins.
The reaction of anilines and phenylacetaldehydes in the presence of chiral phosphoric acid afforded optically active 1,2-trans, 2,3-cis 1,3-diaminotetralins in high yields with excellent diastereo- and enantioselectivities. The trans/cis product was readily isomerized to a trans/trans stereoisomer with no significant loss of enantiomeric purity.
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS , 91198 Gif-sur-Yvette Cedex, France.
Guillaume
G
Dagousset
William
W
Erb
Jieping
J
Zhu
Géraldine
G
Masson
D000079:Acetaldehyde / Q000031:analogs & derivatives / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
D009570:Nitriles; D010756:Phosphoric Acids; D013764:Tetrahydronaphthalenes; C030242:phosphoric acid; D000079:Acetaldehyde; C013192:phenylacetaldehyde