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- W2057384518 abstract "Photochemistry of Aminoketones. VIII. Diastereoselective Synthesis of 3-Hydroxy-prolines Glycine esters react in two steps (aminoalkylation and N-acylation) to N-acyl-N-(β-benzoylethyl)-glycine ester 3. In less polar solvents these ketonic compounds are n,π*-excited by 300 nm irradiation. In ether 3* yield mixtures of aminocyclopropanoles 4, hydroxyprolines 5 and products of additions and cleavages. In benzene and cyclohexane/benzene, respectively, the regioselective photocyclization to 5 is favoured. Furthermore this hydroxyproline synthesis has the advantages of high diastereoselectivity yielding the (2,3) E–5 and of high overall-yields in connection with the one pot method. The influence of solvents and substituents on the regio- and diastereoselectivity are explained using a model with stabilization of special conformations of intermediates by dipol-dipol interactions." @default.
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- W2057384518 date "1985-01-01" @default.
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- W2057384518 title "Photochemie von Aminoketonen. VII. Eine diastereoselektive Synthese von 3-Hydroxy-prolinen" @default.
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- W2057384518 doi "https://doi.org/10.1002/prac.19853270108" @default.
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