Development of catalytic enantioselective amide allylation of isatins under mild conditions and its application to the synthesis of spirocyclic 2-oxindole lactones
Project/Area Number |
25410038
|
Research Category |
Grant-in-Aid for Scientific Research (C)
|
Allocation Type | Multi-year Fund |
Section | 一般 |
Research Field |
Organic chemistry
|
Research Institution | Shizuoka University |
Principal Investigator |
Yoda Hidemi 静岡大学, 工学部, 教授 (20201072)
|
Co-Investigator(Kenkyū-buntansha) |
TAKAHASHI MASAKI 静岡大学, 工学部, 教授 (30313935)
SENGOKU TETSUYA 静岡大学, 工学部, 助教 (70451680)
|
Project Period (FY) |
2013-04-01 – 2016-03-31
|
Project Status |
Completed (Fiscal Year 2015)
|
Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
|
Keywords | イサチン / アミドアリル化 / 不斉触媒 / 立体選択性 / 生理活性物質 / ジカルボニル化合物 |
Outline of Final Research Achievements |
Novel catalytic asymmetric amide allylation of isatin derivatives with β-amido functionalized allylstannanes was investigated to develop an enantioselective synthesis of antineoplactic spirocyclic 2-oxindole lactones. As a result of our investigations, we found that indium-catalyzed amide allylation of isatins with N-(p-tolyl)-β-amidoallylstannane provided the corresponding homoallylic alcohols with both excellent enantioselectivities and chemical yields. Several mechanistic investigations demonstrated that the substrate-reagent hydrogen bond interaction plays a critical role in the formation of the key transition state resulting in enhanced catalytic reactions. Subsequent lactonization of the homoallylic alcohols followed by iodination gave the corresponding spirocyclic 2-oxindole lactones without loss of the stereochemical integrities.
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Report
(4 results)
Research Products
(65 results)