Abstract
The regiochemistry of aza-annulation of enaminones with alpha,beta-unsaturated acid chlorides bearing hydrogen atoms on the gamma-carbon is reversed when triethylamine is used as mediator. When the reaction was carried out at lower temperatures as 3-acyl beta,gamma-unsaturated compound could be isolated which cyclised to the desired product under thermal or basic conditions. The nature of this intermediate strongly suggests that a vinyl ketene is the active acylating agent. (C) 1997 Elsevier Science Ltd.
| Original language | English |
|---|---|
| Pages (from-to) | 11827-11834 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 53 |
| Issue number | 34 |
| Publication status | Published - 25 Aug 1997 |
Keywords
- ALKALOIDS
Cite this
Murphy, JP., Hadden, M., & Stevenson, PJ. (1997). Aza-annulation of enaminones with crotonyl chloride - Formal reversal of regioselectivity. Tetrahedron, 53(34), 11827-11834.