Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octa-hydroindole-2-carboxylic acid, a new fused proline

Abstract

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] 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). © Georg Thieme Verlag Stuttgart.We thank the Spanish National Research Council (CSIC. Project PIE-200880I260), the Ministry of Science and Innovation (MICINN, Madrid; Projects CTQ2009-09028, CTQ2010-19606, and CTQ2010-17436) and the Government of Aragón (Zaragoza; Project PI064/09 and Research Groups E-10 and E-40) for financial support of our research. R.P.H. thanks the Aragón I + D Foundation for her permanent contract.Peer Reviewe