Stereocontrolled synthesis of 2,5-disubstitutedtetrahydrofurans2,5에 치환체가 있는 테트라하이드로퓨란의 입체선택적 합성

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Structurally complex tetrahydrofuranyl derivatives are often found in nature, some of which show a variety of biological activities. One of the most effective approaches to tetrahydrofurans is electrophile-mediated cyclization of $\gamma$-hydroxyalkenes. One of the concerned issues for these reactions is the stereochemistry of newly formed stereogenic centers. Since they are formally a 5-Exo-Trig favored process, a stereogenic center can be introduced to the exocyclic side chain. If the 5-Endo disfavored process of $\beta$-hydroxyalkenes is achieved in a stereocontrolled manner, it can be complementary to the above 5-Exo favored process due to feasible creation of endocyclic stereogenic centers to tetrahydrofurans. In this context we performed iodoetherification of 4-(3 $^\prime$ furanyl)-3-butenol derivatives. The best reaction conditions for anti-2,5-disubstituted tetrahydrofuran were achieved by using iodine(5eq.) with potassium carbonate(2eq.) in diethyl ether at -78$^\circ$C, and the corresponding syn-isomer was obtained when substrate and triethylamine(0.5eq.) in acetonitrile were added dropwise to the solution of iodine(10eq.), potassium carbonate(2eq.) and tbutanol(4eq.) in acetonitrile at 0$^\circ$C.
Advisors
Kang, Sung-Horesearcher강성호researcher
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1993
Identifier
68369/325007 / 000911436
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1993.2, [ ii, 59 p. ]

URI
http://hdl.handle.net/10203/32639
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=68369&flag=dissertation
Appears in Collection
CH-Theses_Master(석사논문)
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