Chiral bifunctional organocatalysts bearing a 1,3-propanediamine unit for the aza-MBH reaction

The introduction of a 1,3-propanediamine unit at the 3-position of (S)-BINOL using a methylene spacer led to the formation of a chiral bifunctional organocatalyst for the aza-Morita–Baylis–Hillman (aza-MBH) reaction. The organocatalyst 1k mediated aza-MBH transformations with high chemical yields and with up to 82% ee.

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(S)-3-(N-Benzyl-N-3-(pyrrolidin-1-yl)propylaminomethyl)−1,1′-bi(2-naphthol)C35H36N2O2ee = >99%[α]D20=-30.6 (c 0.59, CHCl3)Source of chirality: (S)-BINOLAbsolute configuration: (S)