Abstract:A nickel-catalyzed asymmetric inverse-electron-demand Diels-Alder reaction of N-sulfonyl-1-aza-1,3-dienes with vinyl ethers leads to functionalized piperidines. A Lewis acidic nickel complex, Ni(ClO4)...A nickel-catalyzed asymmetric inverse-electron-demand Diels-Alder reaction of N-sulfonyl-1-aza-1,3-dienes with vinyl ethers leads to functionalized piperidines. A Lewis acidic nickel complex, Ni(ClO4)2, is required in 10 mol% and the DBFOX-Ph ligand provides good yields, high endo selectivities and excellent enantiocontrol. Variations in the position of the azadiene are generally well tolerated; variations in the vinyl ether and especially substitutions at the iminic carbon are more problematic. To illustrate the synthetic utility of the products, Lewis acid mediated nucleophilic displacement of the alkoxy group and subsequent trapping with a hydride or Grignard reagent affords chiral [1,2,4]benzothiadiazine-5,5-dioxides, which are potential drugs for memory/learning disorders and neurodegenerative diseases.Read More
Publication Year: 2007
Publication Date: 2007-03-23
Language: en
Type: article
Indexed In: ['crossref']
Access and Citation
AI Researcher Chatbot
Get quick answers to your questions about the article from our AI researcher chatbot