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Cyclofunctionalisation of epoxyalcohol derivatives. 2. Stereo- and regiospecific conversion to 1,3-dioxolanes

✍ Scribed by Stuart W McCombie; William A Metz

Book ID: 104227389
Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 179 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95734-4

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✦ Synopsis

2,3-Epoxyalcohols react with paraformaldehyde and either cesium carbonate or potassium carbonate/phase-transfer catalyst in polar, aprotic solvents to give excellent yields of 4-(1-hydroxyalkyl)-1,3-dioxolanes, with inversion at C-2. Carbonates and carbamates of 2,3-epoxyalcohols undergo cyclisation induced by protic or Lewis acids, delivery of oxygen to C-2 being the dominant result2. A thorough study by

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