✦ LIBER ✦
γ-Silylated α,β-unsaturated amides. Formation by [1,5] silicon migration from O-silylated vinyl ketene aminals and fluoride- and Lewis acid-mediated aldol condensations
✍ Scribed by J.R. Green; M. Majewski; B.I. Alo; V. Snieckus
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 278 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
0-Silylated vinyl ketene aminal 2, obtained from lithiated unsaturated amide 1, undergoes a thermal [1,5] silicon migration to give y-silylated product 3b which participates in fluoride-and titanium tetrachloride-mediated aldol condensations to give adducts 5 in poor and excellent syn diastereoselectivity respectively.