Titanium tetrachloride promoted reaction of silyl ketene acetals with epoxides: a new method for the synthesis of γ-butanolides
✍ Scribed by Veselin Maslak; Radomir Matović; Radomir N. Saičić
- Publisher
- Elsevier Science
- Year
- 2002
- Tongue
- French
- Weight
- 65 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A new method for the synthesis of g-butanolides is described. The titanium tetrachloride promoted reaction of silyl ketene acetals with epoxides, followed by acidic work-up, affords the corresponding butyrolactones in 44-83% yield.
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Asymmetric synthesis of 8-lactams by means of the reaction of dimethylketene silyl acetal with (S)-alkylidenetl-arylethyl)amines in the presence of titanium tetrachloride was studied. The extent of the asymmetric induction was in the range of 44-78% (diastereomeric purity 72-898) and the (S)-configu