## Methyl 4-(5-nitro-1,3-dioxaspiro[5.5] undecan-5-yl)but-2-enoate 2, obtained from the palladium(0)-catalyzed reaction of a salt of 5-nitro-1,3-dioxane 1 with methyl g-bromocrotonate, was converted into the title piperidinone (ee 78%) in three steps.
SYNTHESIS OF 5-HYDROXYMETHYL-1,4-DIOXAN-2-ONE
β Scribed by Broggini, Gianluigi; Zecchi, Gaetano
- Book ID
- 127178633
- Publisher
- Taylor and Francis Group
- Year
- 1991
- Tongue
- English
- Weight
- 178 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0030-4948
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π SIMILAR VOLUMES
Almost equal amounts of the trans and cis isomers of 2,5-diethoxy-2,5-bis(hydroxymethyl)-1,4dioxane (2trans and 2cis) are obtained by treating dihydroxyacetone with acidic ethanol. To explain the formation of an unusually large quantity of 2cis, conformation analyses and equilibration experiments we
Selective transformations of diethyl (R)-malate afforded (R)-4-hydroxymethyl-2,2-dimethyl-l,3-dioxane 7 in reasonable yield. Subsequent synthesis of (2S,6R,8S)-2,8dihydroxyethyl-1,4,7,10-tetraoxaspiro[5.5]undecane 11 was achieved using precursor 7.