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Preparation of 1-Methoxycarbonyl-1-t-Butyldimethylsilyloxy Epoxides. Their Transformation into 3-Hydroxy 2-Acetal-Esters and certain 3-Hydroxy 2-Keto-Esters

โœ Scribed by Bernard Pujol; Richard Sabatier; Pierre-Alexandre Driguez; Alain Doutheau


Book ID
104224711
Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
287 KB
Volume
33
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The peracid oxidation of methyl 2-(t-butyldimethylsilyloxy)-7.alkcnoates 2 furnished the corresponding epoxides 3 in good yields.The regiospecific opening of the latter compounds with methanol afforded 3-hydroxy Z-acetal-esters 4. When alkyl disuhstitnted in position 3, compounds 3 or 4 could be deprotectcd to give rise to 3-hydroxy Z-keto-esters 5.


๐Ÿ“œ SIMILAR VOLUMES


Preparation of 4-hydroxy-3-substituted,
โœ Sharon E. Davis; A. Cameron Church; Rebecca C. Tummons; Charles F. Beam ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Journal of Heterocyclic Chemistry ๐ŸŒ English โš– 305 KB

## Abstract C(ฮฑ)โ€Carboxylic acid esters were treated with excess lithium diisopropylamide, condensed with methyl salicylates or methyl thiosalicylate, followed by acid cyclization to either 4โ€hydroxyโ€3โ€substituted, 2__H__โ€1โ€benzopyranโ€2โ€ones (coumarins), or 2__H__โ€1โ€benzothiopyranโ€2โ€ones (thiocouma