Synthesis On Chiral Amines

This thesis is focused on the synthesis of chiral ferrocenyl amines and chiral 2, 2'-substituted 1,1'-binaphthyl ligands. These novel compounds were identified and characterized by NMR and MS spectra. The main research results are as follows:1. Lla, Lla' were obtained from the condensation of carboxyaldehyde ferrocene with N-Boc-(S)-2-amine methyl pyrrolidine and N-Boc-(R)-2-amine methyl pyrrolidine, respectively,and following deprotection of Boc group. L1b, L1b' were provided by methylation of the products from the reaction of carboxyaldehyde ferrocene reacted with N-Boc-(S)-2-amine methyl pyrrolidine and N-Boc-(R)-2-amine methyl pyrrolidine, and following deprotection of Boc group.2. L2a and L2a'were prepared by the reaction of 1,1'-dicarboxyaldehyde ferrocene with N-Boc-(S)-2-amine methyl pyrrolidine and N-Boc-(R)-2-amine methyl pyrrolidine and treatment with 5N HC1 to remove Boc group. The products from the reaction of 1,1'-dicarboxyaldehyde ferrocene with N-Boc-(S)-2-amine methyl pyrrolidine were methylated and treated by 5N HC1 to give L2b; The products from the reaction of 1,1'-dicarboxyaldehyde ferrocene with N-Boc-(S)-2-amine methyl pyrrolidine were methylated and reducted by LiAlH4 to give L2c. 3. (R)-1,1'-binaphthalenyl-2,2'-dicarbaldehyde was obtained by the reaction of (R)-BINOL, which after chlorosulfonation, methylated, bromination, formylation, and the reaction of (R)-1,1'-binaphthalenyl-2,2'-dicarbaldehyde with N-Boc-(S)-2-Amine methyl pyrrolidine was followed, and eventually be deprotected to generate L3.