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- W2024653913 abstract "An enantiospecific synthesis of (S)- and (R)-(E)-5-[1-cyclohexyl-3-phenyl-2-(imidazol-1-yl)propylidene]aminooxypentanoic acids 2 using homochiral phenylalanines as starting material is described. Protected α-hydroxy-N,O-dimethylamides 4, obtained from α-hydroxyacids 3 were coupled with 1-cyclohexenyllithium to afford α,β-enones 5, which were in turn converted to α-hydroxyketones 6. Configurational liability of compound 11, prompted us to attempt imidazole introduction on the α-hydroxy-O-alkyloxymes 12 which proved to be configurationally more stable. Thus nucleophilic substitution on α-mesyloxy-O-alkyloxymes 14 led, after ester removal, to homochiral compounds 2. The use of hydrogenolysis for 14b deblocking provided 2a with 97% ee. Considerations on the stereochemical outcome of this hitherto undescribed nucleophilic substitution on α-mesyloxy-O-alkyloxymes are reported." @default.
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- W2024653913 date "1997-01-01" @default.
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- W2024653913 title "Nucleophilic substitution on α-mesyloxy-O-alkyloximes—II. Enantiospecific synthesis of 2-(imidazol-1-yl)-1-cyclohexyl-3-phenylpropan-1-one O-alkyloximes" @default.
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- W2024653913 doi "https://doi.org/10.1016/s0957-4166(96)00506-x" @default.
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