Abstract
α-Hydroxyphosphonates (±)- 3 were prepared and transformed into esters (±)- 5. Eight lipases as well as pig liver esterase were tested as catalysts for enantioselective hydrolyses of α-(acyloxy)phosphonates in a biphasic system. Two of them proved to be useful. The highest enantioselectivity was obtained with lipase F-AP 15 and α-(acetyloxy)phenylmethylphosphonates(±)- 5a and (±)- 5b as substrates. The (S)-enantiomers were exclusively hydrolyzed to give optically pure alcohols (S)-(−)- 3a and (S)-(−)- 3b. Lipases AP 6 and F-AP 15 were used to prepare phosphonates (S)-(−)- 3b, (S)-(+)- 3d and (S)-(−)- 3e on a preparative scale with an enantiomeric excess of 81%, 87%, and 89%, respectively. The absolute configurations ofthe α-hydroxyphosphonates were assigned by Horeau's method and 1H-NMR spectroscopy of Mosher's derivatives.
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