Asymmetric reaction using new chiral auxiliaries and catalysts synthesized from (S)-indoline-2-carboxylic acid = (S)-인돌린-2-카르복실산으로부터 합성되는 새로운 키랄보조기와 키랄촉매를 이용한 비대칭 반응

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New chiral auxiliaries and catalysts and have been synthesized from (S)-indoline-2-carboxylic acid and found to provide high stereoselectivities in various asymmetric reactions. New chiral acrylamides were prepared to examine 1,3-dipolar cycloaddition with nitrile oxides. The nitrile oxides cycloadditions to dipolarophiles gave chiral 2-isoxazolines with high diastereoselectivities (up to 95 : 5). Asymmetric Diels-Alder reactions of new chiral dienophiles with 1,3-dienes proceeded with high opposite diastereofacial selectivity in both endo-S and endo-R (up to 99 : 1ds, respectively) depending upon Lewis acids and the structures of chiral auxiliaries. Diastereoselective allylations of new chiral α-keto amides were examined by allylating reagents (allyl-silane and-stannane) in the presence of Lewis acids to result in extremely high diastereoselectivities (up to 99% de). Simmons-Smith cyclopropanation of cinnamyl alcohol with $Et_2Zn$ and $CH_2I_2$ in the presence of new chiral amino alcohols afforded high enantioselectivity (up to 82% ee). Stereoselective β-masked formylation of 1,3-dioxolan-2-yl radical to new chiral a,b-unsaturated amides using $(n-Bu_4N)_2S_2O_8$ showed fairly good levels of asymmetric inductions (up to 85 : 15). Enantioselective addition of lithium diethyl phosphite to imine in the presence of chiral ligands afforded modest enantioselectivities (up to 50% ee).
Advisors
Kim, Yong-Hae김용해
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1996
Identifier
105349/325007 / 000935051
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1996.2, [ ix, 171 p. ]

Keywords

Chiral Auxiliaries; Asymmetric Reaction; Chiral Catalysts; 키랄 촉매; 키랄보조기; 비대칭 반응

URI
http://hdl.handle.net/10203/31429
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=105349&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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