| Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
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| Outline of Final Research Achievements |
We developed a three-step synthesis of multi-substituted amines from N-alkoxyamides. Utilization of the N-alkoxy group as a reactivity control element was the key to success in this three-step synthesis. The first reaction was the N-alkoxyamide/aldehyde coupling reaction. The N-alkoxy group of amides enhanced the nucleophilicity of the nitrogen, enabling the direct coupling reaction. The second reaction was nucleophilic addition to the N-alkoxyamides. Incorporation of the N-alkoxy group into the amides increased the electrophilicity of the amide carbonyls and promoted the chelation effect. The third reaction was electrophilic amination using the resulting N-alkoxyamines. The developed method was applicable to a variety of substrates, resulting in the elaboration of multi-substituted amines including complex alkaloids such as fasicularin.
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