Asymmetric aldol reactions of isatins catalyzed by phthalimido-prolinamide

Enantioselective aldol reactions of isatins with acetone using phthalimido-prolinamide organocatalyst 1 are described. The protocol was effective under solvent free and additive free reaction conditions with 20 mol % of 1 leading to the desired aldol products in good yields and with good enantioselectivities.

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(S)-3-Hydroxy-3-(2-oxopropyl)indolin-2-oneC11H11NO3[α]D20 = −24.1 (c 1, CH3OH)Source of chirality: asymmetric aldol reactionAbsolute configuration: (S)