The asymmetric synthesis of chiral cyclic α-hydroxy phosphonates and quaternary cyclic α-hydroxy phosphonates.
A highly practical, catalytic enantioselective cyclic phosphite addition to aldehydes and ketones was developed. The reaction rate of the asymmetric hydrophosphonylation was significantly enhanced by the addition of silver carbonate. Particularly, significant improvement has been achieved on the asymmetric hydrophosphonylation of unactivated ketones, giving quaternary α-hydroxy phosphonates with excellent enantioselectivity (up to 99% ee).
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei, 430079, P. R. China.
Chubei
C
Wang
Chao
C
Xu
Xiaosong
X
Tan
Hao
H
Peng
Hongwu
H
He
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D006571:Heterocyclic Compounds; D007659:Ketones; D063065:Organophosphonates