Stabilized Chiral Organic Material Containing BINAP Oxide Units as a Heterogeneous Asymmetric Organocatalyst for Allylation of Aldehydes

Condensation of BINAPO-(PhCHO)₂ and 1,3,5-tris(4-aminophenyl)benzene (TAPB) results in a new imine-based chiral organic material (COM) that can be further post-functionalized through reductive transformation of imine linkers to amines. While the imine-based material does not show the necessary stability to be used as a heterogeneous catalyst, the reduced amine-linked framework can be efficiently employed in asymmetric allylation of different aromatic aldehydes. Yields and enantiomeric excesses found are comparable to those observed for the molecular BINAP oxide catalyst, but importantly, the amine-based material also permits its recyclability.