Transformation of Amides by Using an N-Alkoxy Group as a Reactivity Control Element
| Project/Area Number |
15K05436
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Multi-year Fund |
|---|
| Section | 一般 |
|---|
| Research Field |
Organic chemistry
|
|---|
| Research Institution | Keio University |
|---|
Principal Investigator |
Sato Takaaki 慶應義塾大学, 理工学部(矢上), 准教授 (70509926)
|
|---|
| Project Period (FY) |
2015-04-01 – 2018-03-31
|
| Project Status |
Completed (Fiscal Year 2017)
|
| 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)
|
|---|
| Keywords | アミド / 反応性制御素子 / 天然物合成 / 求核付加反応 / 求電子的アミノ化 / 反応性制御 / 天然物化学 / 全合成 / 有機化学 / ヘテロ原子 / 含窒素化合物 / 銅触媒 |
|---|
| 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.
|
Report
(4 results)
Research Products
(53 results)
-
-
-
-
-
-
-
-
-
-
-
-
-
-
[Journal Article] Synthesis of Paclitaxel. 1. Synthesis of the ABC-Ring of Paclitaxel by SmI2-Mediated Cyclization2015
Author(s)
Fukaya, K.; Tanaka, Y.; Sato, A.; Kodama, K.; Yamazaki, H.; Ishimoto, T.; Nozaki, Y.; Iwaki, Y.; Yuki, Y.; Umei, K.; Sugai, T.; Yamaguchi, Y.; Watanabe, A.; Oishi, T.; Sato, T.; *Chida, N.
-
Journal Title
Organic Letters
Volume: 17
Issue: 11
Pages: 2570-2573
DOI
Related Report
Peer Reviewed / Int'l Joint Research
-
[Journal Article] Synthesis of Paclitaxel. 2. Construction of the ABCD-Ring and Formal Synthesis2015
Author(s)
Fukaya, K.; Kodama, K.; Tanaka, Y.; Yamazaki, H.; Sugai, T.; Yamaguchi, Y.; Watanabe, A.; Oishi, T.; *Sato, T.; *Chida, N.
-
Journal Title
Organic Letters
Volume: 17
Issue: 11
Pages: 2574-2577
DOI
Related Report
Peer Reviewed / Int'l Joint Research
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
[Presentation] (±)-ファシクラリンの全合成2017
Author(s)
小林昂弘、南川亮、山本梓央、佐藤隆章、千田憲孝
Organizer
日本化学会第97春季年
Place of Presentation
慶應義塾大学日吉キャンパス（神奈川県・横浜市）
Year and Date
2017-03-16
Related Report
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
