Tetrahedron p. 1183 - 1192 (1985)
Update date:2022-08-05
Topics:
Whitman, Christian P.
Craig, J. Cymerman
Kenyon, George L.
The (+)- and (-) enantiomers of potassium α-phenylglycidate, an irreversible inhibitor of the enzyme mandelate racemase, were synthesized by resolution of the diastereomeric esters with R-(-)-2-octanol.Base-catalyzed ring-opening of the resolved α-phenylglycidate esters gave the enantiomers of 2,3-dihydroxy-2-phenylpropaonic acid, also obtained by resolution of the racemic dihydroxy acid using ephedrine.A comparison of the chiroptical properties of the esters of α-phenylglycidic and 2,3-dihydroxy-2-phenylpropionic acids with those of the structurally similar atrolactic and mandelic acids and their 2-methoxy-derivatives showed that the (-)-methyl 2,3-dihydroxy-2-phenylpropanoate corresponding to the (+)-enantiomer of potassium α-phenylglycidate, as well as the esters of α-phenylglycidic acid derived from the same (+)-potassium salt, were all configurationally related to S-(+)-atrolactic and mandelic acids.The configurational assignments made on the basis of the chiroptical data were confirmed by lithium aluminium hydride reduction of the (-)-2-octyl S- and R-α-phenylglycidates, which led exclusively to the R-(-)- and S-(+)-2-phenyl-1,2-propanediols, respectively, previously related configurationally to R-(-)- and S-(+)-atrolactic acids.
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Doi:10.1016/S0040-4039(00)94771-3
(1985)Doi:10.1002/ardp.19853180602
(1985)Doi:10.1002/jlac.198519850713
(1985)Doi:10.1016/0022-328X(85)87221-1
(1985)Doi:10.1007/BF00948055
(1985)Doi:10.1016/S0040-4039(00)98143-7
(1985)