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Ring Opening of 1,5-Dioxaspiro[3.2]hexanes:  Selective Preparation of α-Heterofunctionalized-β‘-hydroxy Ketones or 2,2-Disubstituted Oxetanes

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journal contribution
posted on 31.08.1999, 00:00 by Amy R. Howell, Albert J. Ndakala
2-Methyleneoxetanes have been converted into 1,5-dioxaspiro[3.2]hexanes with dimethyldioxirane. Reaction of the dioxaspirohexanes with a range of heteroatom nucleophiles, hydride donors, or organoaluminum reagents was successful under neutral or mild conditions, affording, selectively, polyfunctionalized ketones or 2,2-disubstituted oxetanes.