Highly enantioselective synthesis of α-fluoro-α-nitro esters via organocatalyzed asymmetric Michael addition

Primary amines catalyzed the asymmetric Michael addition of ethyl 2-fluoro-2-nitroacetate to enones to provide chiral α-fluoro-α-nitro ester ketones with two contiguous stereogenic centers, one of which is a fluorinated quaternary chiral center, with excellent enantioselectivities and in moderate to good yields.

Graphical abstractDownload full-size imagePrimary amines perform as efficient organocatalysts for the asymmetric addition of α-fluorinated nitroacetate to enones, giving the Michael adducts with two contiguous stereogenic centers, one of which is a fluorinated quaternary chiral center in good to excellent yields and enantioselectivities.