l-Proline derived triamine as a highly stereoselective organocatalyst for asymmetric Michael addition of cyclohexanone to nitroolefins

l-Proline derived triamine 4 has been developed as a highly efficient and stereoselective organocatalyst for the asymmetric Michael addition of cyclohexanone to nitroolefins. In the presence of (CF3SO2)2NH, 4 catalyzed the reaction of cyclohexanone to a variety of nitroolefins with high yields (up to 99%) and excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to 98% ee).

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(2S,4S)-2-Pyrrolidin-1-ylmethyl-4-pyrrolidin-1-yl-pyrrolidineC13H25N3Ee = 100%[α]D20=+5.0 (c 0.70, CH2Cl2)