Anionic cyclization of N-aziridinyl imines = N-아지리디닐 이민의 음이온 고리화반응

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Anionic cyclization, widely utilized for the construction of carbocycles, primarily involve stabilized anionic intermediates, although much attention has recently been devoted to the cyclization of reactive anionic intermediates onto unactivated alkenes. A conceptually novel anionic cyclization has been studied using N-aziridinylimines as 1,1-dipoles. Anionic cyclization reaction of N-aziridinylimines was achieved, involving the formation of consecutive carbon-carbon bonds at the same carbon, which has considerable synthetic potential for the construction of carbocycles. In order to find proper nucleophiles which can reductively alkylate N-aziridinylimine, several nucleophiles were studied and found that vinylmagnesium bromide and allyl lithium gave most satisfactory results. The addition of organometallic reagents such as vinylmagnesium bromide and allyllithium onto N-aziridinylimines generates allyl and homoallyl anions which undergo anionic cyclizations for ring formations. With the evolution of nitrogen and styrene, successive carbon-carbon bond formations at the iminyl carbon of aldehydeaziridinylimine resulted in carbocycle in good yield. Next, tandem anionic cyclization of N-aziridinylimines could be achieved using allyl lithium and vinyl lithium to afford polycarbocycles.
Advisors
Kim, Sung-Gakresearcher김성각researcher
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
2002
Identifier
174668/325007 / 000975209
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2002.2, [ iii, 136 p. ]

Keywords

anionic cyclization; aziridinyl imine; 이민; 음이온고리화반응; 아지리딘

URI
http://hdl.handle.net/10203/31577
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=174668&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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