Synthesis of (S)-2-amino-1,1-diphenylbutan-4-ol; conversion of an α-amino acid into an α-(diphenylmethyl) amine without loss of optical purity

Article abstract of DOI:10.1016/0957-4166(95)00373-W

The title amino-alcohol 4 is an intermediate for the preparation of chiral bicyclic amidines and guanidines, and also for polyamines with potential as ligands in enantioselective catalysis. It has been synthesized from (S)-methionine 1 via (S)-homoserine lactone 2 and amino-diol 3. Hydrogenolysis of the doubly benzylic hydroxyl group in 3 proved non-trivial, but was eventually achieved through the application of catalytic transfer methodology to the bis-acetyl derivative 14.