Design and Application of A Novel Chiral Thioether-phosphoramidite Ligand
Feng Bin, LIN Yao, LIN Shuyu, PENG Liyan, ZHANG Xuelian, YOU Geyun*
Key Laboratory of Regional Ecological Environment Analysis and Pollution Control of West Guangxi, College of Chemistry and Environment Engineering, Baise University, Baise 533000, China
Abstract：A novel chiral thioether-phosphoramidite ligand was synthesized by modular assemble protocol, which featured with short steps, multiple decorating sites and stable structure. The catalytic activity of ligand/Pd complex was investigated with asymmetric allylic alkylation reaction of rac-1,3-diphenylallyl acetate and dimethyl malonate. The solvent effect and base effect were examined, then the match/mismatch phenomenon of the axial chirality and point chirality was investigated. Finally, the influence of steric hindrance and electronic property of the sulfide motifs on the benchmark reaction were examined. Under the optimal reaction conditions, the target product can be obtained in -76% ee.
