Organocatalytic Highly Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates

The cross-aldol reaction between enolizable aldehydes and alpha-ketophosphonates was achieved for the first time by using 9-amino-9-deoxy-epi-quinine as the catalyst. beta-Formyl-alpha-hydroxyphosphonates were obtained in high to excellent enantioselectivities. The reaction works especially well with acetaldehyde, which is a tough substrate for organocatalyzed cross-aldol reactions. The products were demonstrated to have anticancer activities.