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37.3.1.1.11 Method 11: Synthesis by Modification of Oxetanes at the Ring

DOI: 10.1055/sos-SD-037-00246

Griesbeck, A. G.; Sokolova, T.Science of Synthesis, (200837465.

Substituents at the oxetane ring can be exchanged under several conditions without cleavage of the oxetane ring. Oxetan-3-ols can be converted into the corresponding trifluoromethanesulfonates by treatment with trifluoromethanesulfonic anhydride and pyridine and then converted into 3-azides by substitution with sodium azide in dimethylformamide.[‌121‌] By hydrogenation of these products, 3-aminooxetane-2-carboxylic acids are obtained, which can be condensed by peptide techniques to give hexameric β-peptide structures.[‌145‌] Diethyl fumarate can be added to oxetanes in the presence of N-hydroxyphthalimide combined with cobalt(II) acetate under oxygen to produce diethyl 2-hydroxy-3-oxetan-2-ylsuccinate.[‌146‌] The oxidation of a 2-phenylated oxetane with sodium periodate in the presence of catalytic amounts of ruthenium(III) chloride furnishes the corresponding oxetane-2-carboxylic acid.[‌53‌]

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