Stereoselective electrochemical transformation of 4-substituted cyclohexanones into cis-5-substituted-2,2-dimethoxycyclohexanols
β Scribed by Michail N. Elinson; Sergey K. Feducovich; Dmitry E. Dmitriev; Alexander S. Dorofeev; Anatolii N. Vereshchagin; Gennady I. Nikishin
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 62 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Electrolysis of 4-substituted cyclohexanones in methanol in the presence of sodium halides in an undivided cell results in the stereoselective formation of cis-5-substituted-2,2-dimethoxycyclohexanols in 70-80% yield.
π SIMILAR VOLUMES
Various analogues of cis-5-amino-6-oxo-2-piperidinemethanol and cis-5-amino-2-piperidinemethanol have been prepared via Diels -Alder reaction of substituted pyrazinones with ethene followed by acid methanolysis of the bridged lactam adducts. Further reduction of the resulting methyl 2-piperidinecarb
Michael-addition of nitromethane anion to 5-ylidene-1,3-dioxane-4-ones 2 gives high yields of 5-(13-nitroalkyl)-l,3-dioxane-4-ones 3 and 4 with a preponderance of 3 (reattack). Hydrogenation of the products in the presence of Raney-Ni affords optically active 4-substituted cis-3-(o~-hydroxyethyl)-py