Asymmetric reactions using the new chiral indoline derivaties = 새로운 광학활성을 갖는 인돌린 유도체를 이용한 비대칭 유기반응

Cited 0 time in webofscience Cited 0 time in scopus
  • Hit : 297
  • Download : 0
Several new indoline and octahydroindole derivatives were synthesized from S-indoline-2-carboxylic acid to use them as chiral auxiliaries and as chiral catalysts in various asymmetric reactions. Diastereoselective reduction ( up to 98 % ee ), alkylation ( up to 98 % ee ), and pinacol coupling reaction ( up to 96 % ee ) of the chiral α-ketoamides 1a and 1b were carried out. The new chiral amide 6b was alkylated with various alkyl halides in high diastereoselectivities ( up to 98 % ee ). Catalytic asymmetric addition of diethylzinc to aldehydes gave the chiral secondary alcohols in high enantiomeric excesses ( up to 97 % ee ) usinf indoline derivatives 6a, 6b, 7a and 7b as chiral catalysts, and the dramatic reversal of the enantiofacial selectivity was observed when octahydroindole derivatives 8a and 8b were used instead of indoline derivatives. Stereocontrolled catalytic asymmetric reductions ( up to 96 % ee ) of alkyl aryl ketones with oxazaborolidines derived from (S)-indoline derivatives 6a and 6b were carried out (S)-indoline derivatives resulted in S-configuration of the secondary alcohols ( up to 96 % ee )and on the contrary, (S)-octahydroindole derivatives 8a and 8b resulted in R- configuration of the secondary alcohols ( up to 90 % ee ).
Advisors
Kim, Yong-Hae김용해
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1995
Identifier
101853/325007 / 000925162
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1995.8, [ viii, 112 p. ]

Keywords

Indoline; Chiral; Ketoamides

URI
http://hdl.handle.net/10203/31421
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=101853&flag=dissertation
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