Synthesis and asymmetric catalytic activity of (1S,1′S)-4,4′- biquinazoline-based primary amines

Article abstract of DOI:10.1016/j.tetasy.2011.01.009

A series of (1S,1′S)-4,4′-biquinazoline-based primary amines were prepared from natural amino acids via a six-step reaction sequence of protection and condensation followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection. These novel amines were screened for the asymmetric ethylation of aryl aldehydes to yield alcohols with an (S)-configuration with enantiomeric excesses (ee) varying from 2% to 95%.