l-Prolinamide-Catalyzed Enantioselective Synthesis of α-Hydroxyphosphonates

Significance

The first organocatalytic cross aldol reaction of ketones with diethyl formylphosphonate hydrate is reported. In the presence of readily available l-prolinamide as catalyst, secondary α-hydroxyphosphonates have been synthesized in moderate to good yields (up to 95%), good dia­stereoselectivity (up to 95:5) and high enantiomeric ratios (up to >99:1). Besides acetone, other unsubstituted aliphatic ketones also participate in this reaction, however with a lower reactivity. Substituted or cyclic ketones may also be used for this cross aldol reaction.