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  • 08월 28일 16시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

Metal Free Approach to Synthesis of Indolines Including Chiral Indoline Derivatives via Diaryliodonium Salts

등록일
2008년 8월 12일 12시 47분 17초
접수번호
1430
발표코드
34P259포 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
금 <발표Ⅲ>
발표형식
포스터
발표분야
유기화학
저자 및
공동저자
장근삼, 신동석, 이자영, 이병세, 지대윤
인하대학교 화학과, Korea
Indoline frameworks are ubiquitous in numerous biologically active alkaloid non-natural and natural products, as well as organic dyes for dye-sensitized solar cells. Especially, chiral indoline derivatives have been important in chiral auxiliaries, chiral catalysts, and biologically active compounds. Although a number of useful methodologies have been developed for synthesis of various substituted indoline ring systems based on intramoleculr or intermolecular metal-catalyzed cyclization or radical process, metal-free approach to synthesis of indoline derivatives remains a challenge due to either toxic or expensive metal salts possesing high sensitivity of air and moisture. We investigated a metal free approach to synthesis of indoline derivatives using diaryliodonium salt without metal. We obtained a N-Boc-5,6-methylenedioxy-indoline from 2-{6-(2,6-dimethoxyphenyl)-benzo[1,3]dioxol-5-yl}-ethyl carbaminic acid tert-butylester iodonium tosylate or 2-{6-(2-thienyl)-benzo[1,3]dioxol-5-yl}-ethyl carbaminic acid tert-butylester iodonium tosylate in the presence of TEMPO. The reactant iodonium salt having wide variety of functional groups such as ether, ester, and acetal groups on the aryl ring was reacted smoothly to give corresponding substituted indolines in good yields. This approach also allows the synthesis of chiral indolines from phenylalanine derivatives.

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