Phosphoric Acid catalyzed diastereo- and enantioselective synthesis of substituted 1,3-diaminotetralins.

Guillaume Dagousset (1) , William Erb (1) , Jieping Zhu , Géraldine Masson (1)

1 ICSN - Institut de Chimie des Substances Naturelles

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.

Domaines: Chimie organique

Guillaume Dagousset, William Erb, Jieping Zhu, Géraldine Masson. Phosphoric Acid catalyzed diastereo- and enantioselective synthesis of substituted 1,3-diaminotetralins.. Organic Letters, 2014, 16 (9), pp.2554-7. ⟨10.1021/ol500946w⟩. ⟨hal-00990947⟩