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Deprotonation of β,β-disubstituted α,β-unsaturated amides - Mechanism and stereochemical consequences

✍ Scribed by Green, James R; Majewski, Marek; Snieckus, Victor

Book ID
111880708
Publisher
NRC Research Press
Year
2006
Tongue
French
Weight
251 KB
Volume
84
Category
Article
ISSN
0008-4042

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Stereoselective deprotonation of α,β-uns
Stereoselective deprotonation of α,β-unsaturated amides
✍ M. Majewski; J.R. Green; V. Snieckus 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 298 KB

Deprotonation of unsaturated amides 3cf occurs stereoselectively from the Z-y -carbon leading, after methylation, to deconjugated products 4-6. An eight membered ring transition state model analogous to the Ireland formulation for enolization is proposed to explain these observations.