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학술발표회초록보기

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제110회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Catalytic Enantioselective Carbon-Carbon Bond Formation of Diazoesters with Aldehydes

등록일
2012년 8월 29일 14시 21분 19초
접수번호
0609
발표코드
ORGN1-2 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
목 09시 : 30분
발표형식
심포지엄
발표분야
유기화학 - Current Trends in Organic Chemistry: Catalysis and Synthesis
저자 및
공동저자
류도현
성균관대학교 화학과, Korea
The chemistry of α-diazocarbonyl compounds has attracted great attention because of its extensive applications in organic chemistry since the first recorded synthesis of ethyl diazoacetate by Curtius in 1883. Recently, we developed highly enantioselective, catalytic carbon-carbon bond formation reactions of diazoesters with aldehydes. Enantioselective cyclopropanation reactions via Michael- initiated ring closure between diazoacetates and α,β-unsaturated aldehydes are highly desirable as the corresponding cyclopropanes containing two or more electron-withdrawing groups can be valuable synthetic intermediates for various applications. In the presence of chiral (S)-oxazaborolidinium cation as catalyst, catalytic synthetic approach to get the highly functionalized cyclopropane was investigated. Reactions proceeded in high yield with high to excellent diastereoselectivity and enantioselectivity. In addition, a catalytic route toward chiral α-alkyl-β-ketoesters using asymmetric Roskamp reaction of α-alkyl diazoester with aldehydes has been developed. The reaction proceeds with high to excellent enantioselectivities and this methodology was applied to a concise two-step synthesis of the natural pheromone sitophilate.

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