Reductive cascade transformations of heteroatom-containing unsaturated molecules by Lewis acid catalysis = 루이스산 촉매 작용을 통한 헤테로원자-포함 불포화 화합물의 연속적 환원 반응에 관한 연구

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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.
Advisors
Chang, Sukbokresearcher장석복researcher
Description
한국과학기술원 :화학과,
Publisher
한국과학기술원
Issue Date
2020
Identifier
325007
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2020.2,[iii, 85 p. :]

Keywords

Lewis acidic boron▼ahydrosilylation▼ahydroboration▼aunsaturated compounds▼astereoselectivity; 루이스 산성 붕소▼a수소화규소 반응▼a수소화붕소 반응▼a불포화 화합물▼a입체선택성

URI
http://hdl.handle.net/10203/283545
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=907056&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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