Control of diastereoselectivity in the aldolization of methyl phenylacetate
✍ Scribed by Sergio Pinheiro; Marcelo B Lima; Clara B.S.S Gonçalves; Sérgio F Pedraza; Florence M.C de Farias
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 92 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The aldolization of methyl phenylacetate with benzaldehyde in several conditions was studied. While the use of LDA in THF-HMPA gave the anti-aldol, the dibutylboron triflate furnished the syn-aldol in high diastereoselectivity (syn:anti=97:3).
📜 SIMILAR VOLUMES
Deprotonation of methyl phenylacetate with lithium diisopropylamide in tetrahydrofuran followed by trapping with trimethylsilyl chloride afforded an 81:19 mixture of E-and Z-silyl ketene acetals in agreement with a prediction by the calculation by Dauben. The E-silyl ketene acetal was readily isomet
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