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  • 02월 19일 10시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제121회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Synthesis of Chiral 3,4-Dihydropyranones through Bioinspired Michael addition/lactonization Reaction Cascade

등록일
2018년 2월 13일 16시 41분 24초
접수번호
6151
발표코드
ORGN.P-566 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
4월 19일 (목요일) 11:00~12:30
발표형식
포스터
발표분야
Organic Chemistry
저자 및
공동저자
HUI JIN, JUYEOL LEE, Do Hyun Ryu*
Department of Chemistry, Sungkyunkwan University, Korea
Dihydropyranones are important structural core of numerous natural or synthetic biologically active compounds. A biomimetic tandem Michael addition-lactonization reaction of thioesters and β,γ-unsaturated α-Keto esters catalyzed by proline derived urea catalyst has been developed for the synthesis of chiral 3,4-dihydropyranones. The reaction provided 3-thioester-substituted 3,4-dihydropyranones and spiro-3,4-dihydrocoumarin-fused 3′,4′-dihydropyranones in high yield (up to 94%) with excellent stereoselectivities (up to >20:1 dr, 99% ee). The high level of stereoselectivities were rationalized by DFT calculations. In addition, the utility of the products was shown in the formal synthesis of anti-hypercholesterolemic agent.

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