Catalytic asymmetric synthesis of quaternary α-hydroxy trifluoromethyl phosphonate via chiral aluminum(III) catalyzed hydrophosphonylation of trifluoromethyl ketones.
The chiral hydrogenated tridentate Schiff base-aluminum(III) complex has been first applied in the catalytic enantioselective hydrophosphonylation of trifluoromethyl ketones. The side reactions related to phospha-Brook rearrangement were completely avoided, and the corresponding quaternary α-hydroxy trifluoromethyl phosphonates have been first synthesized in good yields with high enantioselectivities (up to 90% ee).
Zhou
Xin
X
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.
Zhang
Qi
Q
Hui
Yonghai
Y
Chen
Weiliang
W
Jiang
Jun
J
Lin
Lili
L
Liu
Xiaohua
X
Feng
Xiaoming
X
D000535:Aluminum / Q000737:chemistry*; D002384:Catalysis; D017611:Fluorine Compounds / Q000737:chemistry*; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D008745:Methylation; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D010766:Phosphorylation; D013237:Stereoisomerism
D017611:Fluorine Compounds; D007659:Ketones; D008024:Ligands; D009943:Organophosphorus Compounds; C554302:alpha-hydroxy trifluoromethyl phosphonate; D000535:Aluminum