Regioselective Reduction of 3-Sulfonyl Glutarimides to 3,4-Dihydro-5-sulfonylpyridin-2-ones. Formal Synthesis of the Indolizidine 8a-epi-Dendroprimine.
β Scribed by Ru-Ting Hsu; Li-Ming Cheng; Nein-Chen Chang; Huo-Mu Tai
- Book ID
- 101934084
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 30 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0931-7597
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π SIMILAR VOLUMES
Treatment of N-alkyl-3-sulfonyl glutarimides (1) with sodium hydride and then lithium aluminum hydride could give regioselective reduced hydroxy piperidones (5) which were further dehydrated to 3,4-dihydro-3-tosylpyridin-2-ones (6) in the presence of boron trifluoride.
More recently (q), CsF/Si(OCH3)4 was successfully used for 1,4-addition reactions to cr, B-unsaturated tertiary amides. We now report (see Table > the results 1311
## Abstract We hereby report the first preparation of the 5,6βdihydroβ4__H__βfuro[2,3β__c__]pyrrolβ4βone (**3**) and its derivatives starting from methyl 3β(methoxycarbonyl)furanβ2βacetate (**8**). The ester functionality connected to the methylene group was regiospecifically converted to the desir