膦手性化合物合成及其在查尔酮不对称加成反应中应用.

杨 帅; 杜 鹏; 吕 小 兵

Chiral phosphines-borane adducts are synthesized from dichlorophenylphosphine using L-menthol as a chiral resolution reagent. The two configurations of phosphines-borane adducts exhibit different chemical shifts in the ¹H-NMR spectrum, and can be separated by recrystallization. The single enantiomer is methylated with MeLi to afford single configuration of chiral methylated phosphines borane adduct with retention of configuration, and its molecular geometry is characterized by X-ray crystal structure analysis. Chiral phosphines are transformed into the corresponding chiral phosphine oxides with configuration retention using tert-butyl hydroperoxide (TBHP) as oxidant under certain conditions. In addition, the resultant chiral phosphine ligands are evaluated in the asymmetric addition of Et2Zn and chalcone, affording the corresponding compound with 76% yield, but a low enantioselectivity of 9%.

MALI; MOLECULAR shapes; RESOLUTION (Chemistry); PHOSPHINE oxides; CRYSTAL structure; ADDITION reactions; PHOSPHINES; CHALCONE

Journal of Dalian University of Technology / Dalian Ligong Daxue Xuebao, 2020, Vol 60, Issue 5, p486

1000-8608

Academic Journal

10.7511/dllgxb202005005