Diethylformylphosphonate hydrate

Linear a-hydroxyphosphonates can be synthesized via an L-prolinamide-catalyzed aldol reaction of a ketone with diethylformylphosphonate hydrate. Using chloro-, hydroxy-, or methoxyacetone as nucleophiles, the reaction proceeded in a highly regioselective manner leading exclusively to linear aldols [61]. 

Diethylformylphosphonate hydrate reacts as an acceptor with cyclopentanone (78), giving desired aldol 79 in excellent yield and stereoselectivity. Surprisingly, this reaction can be catalyzed by prolinamide even though it proved to be ineffective for the aldol [61]. 

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