Asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with α-fluoro-β-keto esters.
In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr).
Institute of Chemical Biology, Henan University, Jinming Campus, Kaifeng, Henan, 475004, P. R. China.
Lin
L
Yan
Zhiqiang
Z
Han
Bo
B
Zhu
Caiyun
C
Yang
Choon-Hong
CH
Tan
Zhiyong
Z
Jiang
Morita–Baylis–Hillman carbonates; allylic alkylation; asymmetric catalysis; fluorine; fluoro-β-keto esters; natural product