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Stereoselective Formation of Quaternary Carbon Centers: Alkylation of α,α-Disubstituted Amide Enolates.

✍ Scribed by Jeffrey M. Manthorpe; James L. Gleason

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
33
Category
Article
ISSN
0931-7597

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Stereoselective Formation of Quaternary
Stereoselective Formation of Quaternary Carbon Centers: Alkylation of α,α-Disubstituted Amide Enolates
✍ Jeffrey M. Manthorpe; James L. Gleason 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 97 KB

The stereoselective formation of quaternary carbon centers is one of the most challenging tasks in organic chemistry and can only be achieved using methods which employ some form of carbon ± carbon bond forming reaction. [1] One of the most straightforward methods for the formation of carbon ± carbo

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## Abstract **Going through the phases**: The title reaction was found to proceed by an initial base‐mediated isomerization to allenyl esters and subsequent phase transfer catalyzed alkylation at the α position of the ester (see scheme).magnified image

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## Abstract **Ein mehrphasiger Prozess**: Untersuchungen der Titelreaktion ergaben, dass sie als basenvermittelte Isomerisierung zu Allenylester und anschließende phasentransferkatalysierte Alkylierung an der α‐Position des Esters verläuft (siehe Schema).magnified image