Studies On The Synthesis And Applications Of Chiral Amine-Ligands In Asymmetric Synthesis

In this thesis, chiral amine-ligands were synthesized from cheap and commercially available chiral source. The applications in asymmetric oxidative coupling reaction were initially explored. The main research results are as follows: 1. Chiral L1,L3,L4 were synthesized by reactions of 2-hydroxybenzaldehyde,2, 6-diformyl-4-methylphenol and 1,3-benzenedicarbaldehyde with N-(S)-BOC-2-aminomethyltetrahytropyrrole derived from L-proline. Chiral L2 was obtained by deprotection of BOC group with trifluoroacetic acid. The amine-ligands were characterized by NMR,IR,MS.2. Chiral L5,L6,L7 are synthesized according to the same procedure for L1 using (S)-phenylethylamine,(S)-2-benzylethanolamine as chiral source. The compounds were characterized by NMR,IR,MS. 3. The chiral amine-ligands obtained as co-catalyst with copper were initially studied for asymmetric oxidative coupling reaction of 3-hydroxy-2-naphthalenecarboxylic methyl ester. It was found that the coupling reaction showed low enantioselectivity with 10 mol% CuCl and 11 mol% amine-ligands in air. A low ee value of 21% was obtained for L6.