Enantioselective radical addition reactions = 비대칭 라디칼 부가 반응에 관한 연구

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During the past decade, enantioselective radical reactions have been investigated with great interest. Among the various reaction types, conjugate radical addition to $\alpha - \beta$ unsaturated carbonyl compounds has attracted a great deal of attention because of its synthetic utility. A majority of these reactions utilizes carboxylic acid derivatives. To carry out these reactions one needs the use of an achiral template such as alkylidene malonates, Evans’ oxazolidinones, and the imide group. To extend the scope of achiral template in radical conjugate addition reactions, we have introduced $\alpha$’-hydroxy enone and $\alpha$’-phosphoric enone for the construction of new stereogenic carbon centers. Both templates were successively applied to make new chiral compounds in good yields and enantioselectivities. In case of $\alpha$’-phosphoric enone, two adjacent carbon centers were created at once using allyltributyltin reagent with high diastereo- and enantioseletivities. Despite of stunning progresses in organocatayst, only a few radical reactions were reported using organocatalyst in asymmetric radical chemistry. Among the widely used organocatalysts, a chiral phosphoric acid and phosphoramide were tolerable during radical reactions. 2,4,6-$iPr_3Ph$ substituted binol derived phosphoramide catalyst gave the best result as high as 84% ee in enantioselective radical addition reactions to 4-biphenyl substitued imine. Both electro-withdrawing and donating substituents and the usage of $2^o$ and $3^o$ radical sources didn`t influence the selectivities.
Advisors
Kim, Sung-Gakresearcher김성각researcher
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
2009
Identifier
309372/325007  / 020045864
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2009.2, [ 149 p. ]

Keywords

Enantioselective; Radical; Asymmetric Catalyst; Organocatalyst; 광학활성; 라디칼; 비대칭 촉매; 유기촉매; Enantioselective; Radical; Asymmetric Catalyst; Organocatalyst; 광학활성; 라디칼; 비대칭 촉매; 유기촉매

URI
http://hdl.handle.net/10203/31721
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=309372&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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