Search for the new reactivity of aldehydes : Silyl-Oxa-Prins cyclization and borylative coupling reaction = 알데하이드 반응성에 대한 연구 : 실릴-옥사-프린스 고리화 반응과 붕소화 짝지음 반응 Silyl-Oxa-Prins cyclization and borylative coupling reaction

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1.Br$\o$nsted acid-mediated diastereoselective silyl-oxa-Prins cyclization Multisubstituted tetrahydropyranols is a versatile building block in organic synthesis because of their interesting biological activities. We developed an efficient synthetic route to tetrahydropyranols through diastereoselective silyl-oxa-Prins cyclization of α-silyloxy homoallylsilanes with various aldehydes mediated by Brønsted acids. Synthetically valuable tetrahydropyranol products were obtained in high yields with excellent diastereoselectivities. Both syn and anti diastereomers of tetrahydropyranols were selectively obtained by tuning the olefinic geometry of the homoallylsilane substrates. The procedure is operationally simple and large scale reaction was also smoothly performed under mild conditions. 2.(NHC)Cu-catalyzed Borylative Cross-coupling of Olefin and Aldehyde Functionalized organoboron compounds are useful building block utilized in synthesis of various functional molecules and medicines. We herein present the study of (NHC)Cu-catalyzed borylative cross coupling reaction of styrenic olefins and benzaldehydes. The Borylative cross-coupling were more efficient with the electron-deficient styrenes. However, rather limited substrate scope and poor diastereoselectivity have been revealed as the obvious challenges for the future development of this synthetically useful reaction.
Advisors
Chang, Suk Bokresearcher장석복researcher
Description
한국과학기술원 :화학과,
Publisher
한국과학기술원
Issue Date
2017
Identifier
325007
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 2017.8,[ii, 41 p. :]

Keywords

diastereoselective Prins cyclization; silyl-oxa-Prins cyclization; tetrahydropyran; tetrahydropyranol; oxygen heterocycles▼aaldehydes▼aN-heterocyclic carbene▼acopper catalyst▼aborylative cross-coupling▼athree component reaction; 부분 입체 선택적 프린스 고리화반응▼a실릴-옥사 프린스 고리화 반응▼a테트라하이드로피란▼a테트라하이드로피란올▼a산소 헤테로 고리▼aN-헤테로 사이클릭 카벤▼a구리 촉매▼a붕소화 짝지음 반응▼a3 성분 반응▼a알데하이드

URI
http://hdl.handle.net/10203/243587
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=718755&flag=dissertation
Appears in Collection
CH-Theses_Master(석사논문)
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