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학술발표회초록보기

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제114회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Three-Membered Rings and Triple Bonds as Ideal Starting Materials for Domino Cascades

등록일
2014년 9월 1일 19시 29분 52초
접수번호
1407
발표코드
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발표시간
목 14시 : 10분
발표형식
심포지엄
발표분야
유기화학 - Current Trends in Organic Chemistry II: Metallo-Organic Reaction
저자 및
공동저자
Daniel B. Werz
Technische Universität Braunschweig, Germany, Germany
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승인 1건

Cyclopropanes as well as carbon-carbon triple bonds are systems being high in energy. Therefore, both moieties are ideally suited for a cascade of consecutive reactions (domino reactions). In a first part, domino reactions based on ring-enlargement reactions of donor-acceptor-substituted cyclopropanes are discussed. Aldehyde, ketimines and thioketones are utilized as acceptors whereas ether moieties serve as donor. A rearrangement leads to the respective five-membered rings which tend to eliminate water. As a result, aromatic systems are formed. Depending on the substrate domino cascades are initiated which are able to transform the biscyclopropane derivative 1 in one step into the corresponding quaterpyrrol 2. In a second part, Pd-catalyzed domino reactions starting with triple bonds attached to carbohydrate derivatives 4 are reported to construct a variety of chroman- and isochroman-type structures such as 5. Such domino sequences are also employed to a variety of other processes leading to complex scaffolds in a facile and efficient fashion.


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