Organocatalytic enantioselective Mukaiyama-Mannich reaction of fluorinated enol silyl ethers and cyclic N-sulfonyl ketimines

The first catalytic asymmetric Mukaiyama-Mannich reaction of fluorinated silyl enol ethers and ketimines is developed. Under the catalysis of hydroquinine derived bifunctional urea, cyclic N-sulfonyl ketimines readily react with fluorinated enol silyl ethers to afford benzosultam based C-alpha-tetrasubstituted alpha-amino acid derivatives featuring a fluoroalkyl group in high to excellent yields and stereoselectivities.