Reductive Opening of Cyclopropylogous α-Hydroxy Aldehydes and Ketones by Samarium(II) Iodide. -The regioselectivity of the title reaction is found to be strongly dependant on the substitution pattern of the substrate. In several cases, a tandem cyclopropyl opening-deoxygenation reaction leads to γ-
Reductive opening of cyclopropylogous α-hydroxy aldehydes and ketones by samarium(II) iodide
✍ Scribed by Alex Nivlet; Valérie Le Guen; Luc Dechoux; Thierry Le Gall; Charles Mioskowski
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 198 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
SmI2-HMPA was shown to be an effective reagent for reductive alkylation of 0t-cyano ketones, a useful process for regiocontrol of et,et-dialkylation of ketones.
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## Functionalized cyclopropyl ketones have been found to undergo facile reductive cyclopropane ring opening with samarium (II) diiodide in the presence of a proton source. These reactions were exceedingly rapid, taking place in most cases at -78°C under neutral conditions. An ester group substitut