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

2011    Cakici, Murat; Catir, Mustafa; Karabuga, Semistan; Ulukanli, Sabri; Kilic, Hamdullah

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%. (C) 2011 Elsevier Ltd. All rights reserved.