Highly enantioselective 1,4-addition of diethyl phosphite to enones using a dinuclear Zn catalyst.
Zinc benefits: The first catalytic asymmetric phospha-Michael addition of enones has been developed. Under mild reaction conditions, the gamma-oxo phosphonates could be obtained in high yields (up to 99%) with excellent enantioselectivities (93-99% ee; see scheme). The strategy makes the asymmetric synthesis of biologically important phosphonate compounds more accessible.
Zhao
Depeng
D
State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China.
Yuan
Ye
Y
Chan
Albert S C
AS
Wang
Rui
R
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D017905:Phosphites / Q000737:chemistry*; D010766:Phosphorylation; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D007659:Ketones; D063065:Organophosphonates; D017905:Phosphites; D015032:Zinc