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Preparation of proximal β-hydroxy silyl enol ethers from α,β-epoxyketones using silyllithium reagents

✍ Scribed by Heather K. Baker; Aaron M. Hartel

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
972 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new method for the stereoselective preparation of proximal b-hydroxy silyl enol ethers from a,bepoxyketones using silyllithium reagents has been developed. The reaction is believed to proceed via Brook rearrangement assisted by opening of the adjacent epoxide. A number of a,b-epoxyketones were reacted with methyldiphenylsilyllithium to form the corresponding proximal b-hydroxy silyl enol ethers in good to excellent yield and excellent stereoselectivity.

📜 SIMILAR VOLUMES

Preparation of silyl enol ethers from ac
Preparation of silyl enol ethers from acyloin derivatives using silyllithium reagents
✍ Bradley D. Robertson; Aaron M. Hartel 📂 Article 📅 2008 🏛 Elsevier Science 🌐 French ⚖ 121 KB

A new method for the regioselective preparation of silyl enol ethers from acyloin derivatives using silyllithium reagents has been developed. Both dimethylphenyl-and methyldiphenylsilyllithium were found to be effective, the latter providing greater stereocontrol. The reaction is believed to proceed