New asymmetric reactions using (S)-indoline derivatives(S)-인돌린 유도체를 이용한 새로운 비대칭 반응

Cited 0 time in webofscience Cited 0 time in scopus
  • Hit : 471
  • Download : 0
DC FieldValueLanguage
dc.contributor.advisorKim, Yong-Hae-
dc.contributor.advisor김용해-
dc.contributor.authorYoun, So-Won-
dc.contributor.author윤소원-
dc.date.accessioned2011-12-13T04:29:04Z-
dc.date.available2011-12-13T04:29:04Z-
dc.date.issued2001-
dc.identifier.urihttp://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=169546&flag=dissertation-
dc.identifier.urihttp://hdl.handle.net/10203/31566-
dc.description학위논문(박사) - 한국과학기술원 : 화학과, 2001.8, [ vi, 143 ]-
dc.description.abstractThe new chiral auxiliaries for the stereoselective reactions were synthesized from (S)-indoline-2-carboxylic acid. Chiral hydrazones derived from (S)-indoline reacted with organolithiums at -78℃ in short reaction time within 10 minutes to afford arylated or alkylated chiral hydrazines with extremely high diastereoselectivity (up to > 99% de) and high chemical yields (90-99%). The hydrazines are readily converted to chiral amino alcohols. Lithiated methoxyallene was added to chiral α-keto amides derived from (S)-indoline to give the hydroxyalkylated allenes with high diastereoselectivity (up to > 99% de). The crude reaction products could either be transformed to enones by hydrolysis with HCl or converted into 2,5-dihyro-3-methoxyfuran derivatives, which were hydrolyzed to give 3(2H)-dihydrofuranones. The diastereoselectivity was not changed in transformation to the dihydrofuran derivative. Chiral α-keto amides reacted with lithiated acetylene to afford the quaternary propargylic alcohols with very high diastereoselectivity (up to > 99% de). α-Bromoacrylamides reacted with aldehydes or ketones in the presence of $SmI_2$ to produce Baylis-Hillman reaction type``s products through anionic process in good yields (52-89%). This reaction system could be applied to functionalize at 5-position of pyrimidines. 2-Bromoacrlamides bearing (S)-indoline chiral auxiliary reacted with aldehydes in the presence of $SmI_2$ to give the α-hydroxyalkylacrylamides in good yields but with low diastereoselectivity. The asymmetric reductive homocoupling reaction at the 3-position of α, β -unsaturated amides derived from (S)-indoline with $SmI_2$ resulted in (3R,4R)-dialkyladipamide derivatives with extremely high diastereoselectivities (up to > 99%). When the chiral auxiliary was changed from (S)-indoline derivative to (2S,3aS,7aS)-octahydroindoline derivatives, which were obtained by reduction of benzene ring of indoline to cyclohexane ring, the opposite configuration, (3S,4S)-diethyl...eng
dc.languageeng-
dc.publisher한국과학기술원-
dc.subjectAsymmetric Reactions-
dc.subject(S)-Indoline-
dc.subject인돌린-
dc.subject비대칭 반응-
dc.titleNew asymmetric reactions using (S)-indoline derivatives-
dc.title.alternative(S)-인돌린 유도체를 이용한 새로운 비대칭 반응-
dc.typeThesis(Ph.D)-
dc.identifier.CNRN169546/325007-
dc.description.department한국과학기술원 : 화학과, -
dc.identifier.uid000985240-
dc.contributor.localauthorKim, Yong-Hae-
dc.contributor.localauthor김용해-
Appears in Collection
CH-Theses_Ph.D.(박사논문)
Files in This Item
There are no files associated with this item.

qr_code

  • mendeley

    citeulike


rss_1.0 rss_2.0 atom_1.0