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37.3.1.2.1 Method 1: Ring Opening of Oxetanes

DOI: 10.1055/sos-SD-037-00246

Griesbeck, A. G.; Sokolova, T.Science of Synthesis, (200837466.

Ring opening of oxetanes can proceed by several processes and leads to synthetically interesting saturated or unsaturated products: Nucleophilic ring opening by hydrogen peroxide gives 3-hydroperoxy alcohols, which can be converted into 1,2-dioxolanes;[‌149‌] ring opening with dinitrogen pentoxide gives 1,3-dinitrate esters;[‌150‌] and γ-fluoro alcohols are available from oxetanes and silicon tetrafluoride.[‌151‌] Hydrogenolysis of 3-siloxy-substituted oxetanes in methanol with hydrogen gas and a palladium catalyst gives 1,2-diols;[‌152‌] reductive ring opening with lithium tri-tert-butoxyaluminum hydride leaves the siloxy group intact.[‌153‌] The synthesis of 1,3-methoxy alcohols can be achieved by treatment with ammonium cerium(IV) nitrate in methanol.[‌154‌] Oxetan-3-ylmethanols are reagents for introducing ortho ester protecting groups to carboxylic acids.[‌155‌] An improved reagent for this process is (2,2,3-trimethyloxetan-3-yl)methanol (187), which gives the ortho esters 188 (Scheme 67).[‌156‌]

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