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A method for asymmetric reduction of αand β ketophosphonates using chiral complexes prepared from sodium borohydride and natural aminoacids or tartaric acids was developed. Reduction of α or β ketophosphonates by these reagents led to formation of chiral (S)or (R)hydroxyphosphonates. Reduction of chiral di-(1R,2S,5R)-menthylketophosphonates by the chiral complexes NaBH4/(R,R)-proline or NaBH4/(R,R)-tartaric acid due to the double matched asymmetric induction resulted in increased stereoselectivity of the reaction and led to the formation of hydroxyphosphonates up to 90% ee or higher. Dimenthyl 2-hydroxy-3chloropropylphosphonate was utilized as a chiron for the preparation of a number of biologically active compounds in multigram quantity.

Enantioselective reduction of ketophosphonates using adducts of chiral natural acids with sodium borohydride