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  • 09월 03일 23시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제122회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Redox Neutral Access to a4, a6-Synthons via Sulfoxide-Mediated Oxidation of (Di)enynamides

등록일
2018년 8월 30일 17시 56분 03초
접수번호
2155
발표코드
ORGN.P-277 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 18일 (목요일) 11:00~12:30
발표형식
포스터
발표분야
Organic Chemistry
저자 및
공동저자
Huong Quynh Nguyen , Seunghoon Shin1,*
Hanyang University, Korea
1Department of Chemistry, Hanyang University, Korea

Recently we have developed a robust actvation of ynamides by HNTf2 catalyst enabling oxidive coupling of diverse C-nucleophiles. These umpolung enolate discovery allows for outstanding opportunity for redox-eficient processes and enables novel disconnection approaches through non-traditional methods. We envisioned that oxidation of enynamide would provide dienolium synthon (a4), allowing addition of nucleophilic partners at the γ-position, where the steric hindrance between amide nitrogen (N1R2) and oxidant (OSMe2) moiety may direct the regio-selectivity. Meanwhile, one inherent limitation in the gold- or Brønsted acid-catalyzed oxidation of alkynes is the necessity to use pyridine-derived N-oxides as terminal oxidant which liberates pyridine that undermine atom-economy and potentially inhibits the acid-catalyzed cycle. Employing dimethyl sulfoxide (DMSO) as terminal oxidant led to an efficient γ-selective couplings without intervention of side pathways. In addition to carbon nucleophiles, 1o, 2o-alcohols and tosyl hydrazide could be employed as nucleophiles. Using dienynamides as substrates, ε-addition (a6) could be realized with excellent selectivity.


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