The enantioselective addition of 1-fluoro-1-nitro (phenylsulfonyl) methane to isatin-derived ketimines

Abstract

An asymmetric organocatalytic addition of fluorinated phenyl-sulfonylnitromethane to isatin-derived ketimines was developed. The reaction was efficiently catalyzed by a chiral tertiary amine, cinchonine.

This methodology provides a new type of optically active compound with two adjacent quaternary carbon stereocenters in good yield (up to 96%), with moderate diastereoselectivity (up to 5.7 : 1 dr) and excellent enantioselectivity (up to 98/ 96% ee).

Keywords

• Baylis-Hillman reaction
• n-boc ketimines
• vicinal tetrasubstituted stereocenters
• quaternary carbon centers
• tert-butylsulfinyl ketimines
• vinylogous Mannich reaction
• amino acid-derivatives
• aza-Henry reaction
• asymmetric-synthesis
• medicinal chemistry