Intramolecular Ketone-Nitrile Reductive Coupling Reactions Promoted by Samarium(II) Iodide. -The photochemically induced reaction of keto nitriles of type (I), (III), and (V) with SmI 2 offers an efficient route to prepare monocyclic, fused bicyclic, and bridged Ξ±-hydroxy ketones. 5-exo-Coupling pr
Stereocontrolled intramolecular ketone-olefin reductive coupling reactions promoted by samarium diiodide
β Scribed by Gary A. Molander; Caryn Kenny
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 235 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
The stereocontrolled intramolecular coupling of unsaturated P-ketoesters and pketoamides is reported. Good yields of highly substituted P-hydroxycyclopentanecarboxylates are generated in the process, with substantial and predictable stereochemical control at three contiguous stereocenters.
π SIMILAR VOLUMES
Intramolecular and intermolecular ketone-ester reductive coupling reactions promoted by SmI 2 have been studied. Substituted 2-hydroxy-5-ethoxycarbonylcyclopentanones, 5-ethoxycarbonylcyclopentenones and a-ketols were prepared in moderate to good yields at room temperature or under reflux under neut