Preparation of 1-Methoxycarbonyl-1-t-Butyldimethylsilyloxy Epoxides. Their Transformation into 3-Hydroxy 2-Acetal-Esters and certain 3-Hydroxy 2-Keto-Esters
โ 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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โฆ 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.
๐ SIMILAR VOLUMES
## Abstract C(ฮฑ)โCarboxylic acid esters were treated with excess lithium diisopropylamide, condensed with methyl salicylates or methyl thiosalicylate, followed by acid cyclization to either 4โhydroxyโ3โsubstituted, 2__H__โ1โbenzopyranโ2โones (coumarins), or 2__H__โ1โbenzothiopyranโ2โones (thiocouma