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제122회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Asymmetric Synthesis of Dihydropyranones via Au(I)-Catalyzed Intermolecular [4+2] Annulation of Propiolates and Alkenes

등록일
2018년 8월 30일 17시 51분 12초
접수번호
2150
발표코드
ORGN.P-275 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 18일 (목요일) 11:00~12:30
발표형식
포스터
발표분야
Organic Chemistry
저자 및
공동저자
Kim Hanbyul, Seunghoon Shin*
Department of Chemistry, Hanyang University, Korea

α,β-Unsaturated δ-lactone scaffolds are found in a number of medicinal compounds displaying an array of significant biological activities. Based on the powerful alkynophilic activation of homogeneous Au(I)-catalysis, we recently demonstrated that the dihydropyranones could be assembled in a single step from the intermolecular reaction of propiolates with alkenes. However, achieving high level of enantiocontrol has remained elusive in this class of intermolecular gold(I)-catalyzed coupling. Herein, we report a highly enantioselective synthesis of α,β-unsaturated δ-lactones from [4+2] annulation of propiolates and alkenes in upto 95% ee. Notably, for the desired chiral recognition, the choice of 1,1,2,2-tetrachloroethane as solvent was found to be crucial. Furthermore, an anionic surfactant (SDS) improved the product selectivity in the divergence of the cyclopropyl gold carbene intermediate (Scheme 1).


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