Highly Enantioselective Construction of 3‐Hydroxy Oxindoles through a Decarboxylative Aldol Addition of Trifluoromethyl α‐Fluorinated gem‐Diols to N‐Benzyl Isatins

An organocatalytic asymmetric direct aldol addition reaction that involves cleavage of a carbon–carbon bond through the release of trifluoroacetate was developed. The protocol is wide in scope, generating the desired oxindoles of biological interest in nearly quantitative yields (up to 99 %) with excellent enantioselectivities (up to 98 % ee) and diastereoselectivities (up to 99:1 d.r.).