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Preparation of cyclic ethers via oxidative cyclisation of 2-(4-hydroxyalkyl) and 2-(5-hydroxyalkyl)furans with ddq.

✍ Scribed by Laurence M. Harwood; Jeremy Robertson


Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
165 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis


Reaction of 2-(4-or S-hydroxyalky1Jiuan.s with DDQ leads to the smooth formation of cyclic ethers under neutral conditions, but aromatic analogues do not give useful yields of desired products.


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Diastereoselective synthesis of 2,3,4-tr
✍ JΓΆrg Lüßmann; Dieter Hoppe; Peter G. Jones; Christa Fittschen; George M. Sheldri πŸ“‚ Article πŸ“… 1986 πŸ› Elsevier Science 🌐 French βš– 227 KB

The acid-catalyzed ring opening of the title epoxide 1 takes place at the C-l atom with retention of configuration at C-2 to form 2,3-cis-2-hydroxy-substituted y-lactol deriva= tives 3 In basic media, nucleophiles attack the C-Atom with inversion of configuration yielding 2,3-trans-lactols 5. Oxidat