(1R,2R)-(−)-2-Dimethylamino-1-(4-nitrophenyl)-1,3- propanediol/l-proline cocatalyzed enantioselective Morita–Baylis–Hillman reaction

(1R,2R)-(−)-2-Dimethylamino-1-(4-nitrophenyl)-1,3-propanediol (2) was prepared starting from the readily available precursor of antibiotics chloramphenicol. The combination of compound 2 and l-proline have been found to be an efficient cocatalyst for the asymmetric Morita–Baylis–Hillman (MBH) reaction between methyl vinyl ketone (MVK) and aromatic aldehydes. The corresponding adducts were formed in reasonable chemical yields with good enantioselectivities (up to 82% ee). Performance of parallel cocatalytic reactions with chiral amine 2 and the two enantiomers of proline revealed that it is the proline stereochemistry that determines the configuration of the newly formed chiral center.