Organocatalyzed Michael Addition Reaction by Novel (2R,3aS,7aS)-octahydroindole-2-carboxylic Acid, a New Fused Proline

David Roca-Lopez, Pedro Merino, Javier Sayago, Carlos Cativiela, Raquel P. Herrera. Organocatalyzed Michael Addition Reaction by Novel (2R,3aS,7aS)-octahydroindole-2-carboxylic Acid, a New Fused Proline. Synlett . 2011, Vol. , p. 249-2011.

We present here the results obtained in our study on
organocatalytic enantioselective Michael addition reaction of
acetone to different nitroolefines using (2R,3aS,7aS)-
octahydroindole-2-carboxylic acid ((R,S,S)-Oic, 5) as a new and
suitable catalyst for this process. Computational calculations
support the results obtained with (R,S,S)-Oic versus its diastereomeric
form (S,S,S)-Oic. The final products are obtained in good
yields and moderate enantioselectivities (up to 58% ee).