DC Field | Value | Language |
---|---|---|
dc.contributor.advisor | Chang, Sukbok | - |
dc.contributor.advisor | 장석복 | - |
dc.contributor.author | Kim, Eunae | - |
dc.date.accessioned | 2021-05-11T19:43:06Z | - |
dc.date.available | 2021-05-11T19:43:06Z | - |
dc.date.issued | 2020 | - |
dc.identifier.uri | http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=907056&flag=dissertation | en_US |
dc.identifier.uri | http://hdl.handle.net/10203/283545 | - |
dc.description | 학위논문(박사) - 한국과학기술원 : 화학과, 2020.2,[iii, 85 p. :] | - |
dc.description.abstract | The Lewis acid catalysts have played a significant role in organic synthesis. Tris(penetafluorophenyl)borane $B(C_6F_5)_3$ is one of those Lewis acid catalysts, which has received much attention due to its high reactivity and selectivity. Although a diverse range of organic transformations using Lewis acidic boron have been established, the development of new C-X (X = Si, B, etc.) bond formation is still in infancy. In this regard, this thesis describes the development of the reductive cascade transformations of unsaturated molecules to give new $sp^3$ C-Si or C-B bonds via the Lewis acidic boron catalysis as follows. First, the silylative reductive amination of conjugated aldehydes via a Lewis acidic boron catalysis has been developed for the first time. Unsaturated imines generated through a condensation reaction of a broad range of aldehydes with amines, underwent a new C-Si bond formation under the boron catalyst. The NMR study revealed that the bulkiness of amine has an influence on the catalytic reactivity and selectivity. Second, the boron-catalyzed double hydroboration of quinolines was investigated. This study includes a direct formation of C-B bond at the $\beta$-position to the nitrogen atom via the consecutive borylative reduction of a range of quinolines. This borylated tetrahydroquinolines could be converted to 3-hydroxytetrahydroquinolines upon simple oxidation in one-pot. This study revealed that the stereochemistry of the products was determined by the position of the substituents in quinolines. | - |
dc.language | eng | - |
dc.publisher | 한국과학기술원 | - |
dc.subject | Lewis acidic boron▼ahydrosilylation▼ahydroboration▼aunsaturated compounds▼astereoselectivity | - |
dc.subject | 루이스 산성 붕소▼a수소화규소 반응▼a수소화붕소 반응▼a불포화 화합물▼a입체선택성 | - |
dc.title | Reductive cascade transformations of heteroatom-containing unsaturated molecules by Lewis acid catalysis | - |
dc.title.alternative | 루이스산 촉매 작용을 통한 헤테로원자-포함 불포화 화합물의 연속적 환원 반응에 관한 연구 | - |
dc.type | Thesis(Ph.D) | - |
dc.identifier.CNRN | 325007 | - |
dc.description.department | 한국과학기술원 :화학과, | - |
dc.contributor.alternativeauthor | 김은애 | - |
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