Methoxymethylation of tartrate as a strategy for the synthesis of chiral building blocks

Controlled methoxymethylation of tartrate affords mono- and diMOMtartrates. We took advantage of the particular reactivity of methoxymethylethers and of the conformations of the starting C4 unit, to efficiently synthezise various cyclic methyleneketals (dioxane and dioxolane) or cyclic ethers (oxola...

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Bibliographic Details
Published in:Tetrahedron 1996-06, Vol.52 (25), p.8517-8524
Main Authors: Dulphy, Hervé, Gras, Jean-Louis, Lejon, Tore
Format: Article
Language:English
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Summary:Controlled methoxymethylation of tartrate affords mono- and diMOMtartrates. We took advantage of the particular reactivity of methoxymethylethers and of the conformations of the starting C4 unit, to efficiently synthezise various cyclic methyleneketals (dioxane and dioxolane) or cyclic ethers (oxolane and oxetane). Diethyl-L-tartrate is derived into various chiral building blocks following controlled methoxymethylations of the hydroxy group(s).
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00409-7