서지주요정보
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
서명 / 저자 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 / Sung-Han Kim.
저자명 Kim, Sung-Han ; 김성한
발행사항 [대전 : 한국과학기술원, 1996].
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소장정보

등록번호

8006659

소장위치/청구기호

학술문화관(문화관) 보존서고

DCH 96010

SMS전송

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초록정보

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).

서지기타정보

서지기타정보
청구기호 {DCH 96010
형태사항 ix, 171 p. : 삽도 ; 26 cm
언어 영어
일반주기 Includes appendix
저자명의 한글표기 : 김성한
지도교수의 영문표기 : Yong-Hae Kim
지도교수의 한글표기 : 김용해
수록 잡지명 : "Asymmetric 1,3-dipolar cycloaddition of nitrile oxides to new chiral acrylamides derived from (S)-indoline-2-carboxylic acid". Tetrahedron Letters. Elsevier Science Ltd, 34, pp. 6063-6066 (1993)
수록 잡지명 : "Highly stereoselctive allylation to chiral a-keto amides derived from (S)-indoline-2-carboxylic acid. Asymmetric synthesis of functionalized tertiary homoallyl alcohols.". Tetrahedron Letters. Elsevier Science Ltd, 36, pp. 6895-6898 (1995)
학위논문 학위논문(박사) - 한국과학기술원 : 화학과,
서지주기 Reference : p. 144-151
주제 Asymmetric Reaction
Chiral Auxiliaries
Chiral Catalysts
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