A novel and concise synthetic access to chiral 2-substituted-4-piperidone |
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Authors: | Bai-Ling Chen Bing Wang Guo-Qiang Lin |
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Institution: | 1. Department of Chemistry, Fudan University, Shanghai, 200433, China 2. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China
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Abstract: | A novel and concise synthetic access to enantiopure chiral 2-aryl/alkyl substituted 4-piperidone has been demonstrated. This new route features two key steps: the highly diastereoselective conjugate addition of homochiral lithium amides to trans-β-substituted-α,β-unsaturated methyl esters guaranteed the enantiopurity at 2 position (de >19:1) and the intramolecular attacking of carbanions to methyl esters led to the formation of the piperidone ring. A wide range of substrates, including chiral 2-aryl and 2-alkyl-4-piperidones, were successfully synthesized with modest to high yield. Moreover, some non-chiral 3-substituted-4-piperidones were also synthesized with enhanced ring-formation yield, implicating the versatility of this method in construction of various piperidine rings. |
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Keywords: | chiral -substituted--piperidone homochiral lithium amide diastereoselective conjugate addition lithium-iodine exchange intramolecular carbonyl formation |
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