Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Development of Ferrocene-Containing Metal Catalysts for Asymmetric Synthesis

페로센을 이용한 비대칭 유기합성용 금속 촉매의 개발

  • Oh, Yunghee (Department of Chemistry， Dongeui University) ;
  • Choi, Mi-Jin (Department of Chemistry， Dongeui University)
  • 오영희 (동의대학교 자연과학대학 화학과) ;
  • 최미진 (동의대학교 자연과학대학 화학과)
  • Received : 1999.07.05
  • Accepted : 1999.07.16
  • Published : 1999.08.10
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Abstract

New copper complexes with a ligand, L(L=N,N'-cyclohexane bis(ferrocenylmethylene)amine) which was obtained from ferrocene carboxaldehyde and 1,2-diaminocyclohexane with a mole ratio of 2:1, were prepared and characterized. Those were adapted to asymmetric catalysis. The copper(II) complexes do not work in cyclopropanation of styrene and ethyl diazoacetate but copper(I) complex catalyzes. The Cu(I)LOTf (OTf=trifluorometanesulfonate) shows a good regioselectivity giving high trans to cis ratio of up to 80:20.

페로센 카르복시알데히드와 1,2-diaminocyclohexane을 2:1로 반응시켜 키랄 리간드 L(L=N,N'-cyclohexane bis(ferrocenylmethylene)amine)을 합성하고 이를 구리와 반응시켜 새로운 구리 착물을 합성하였다. 이 착물들을 확인하고 비대칭 유기 합성반응에 촉매로 사용하였다. 구리(II) 착물들은 스티렌과 에틸디아조아세테이트와의 시클로프로판화 반응에서 촉매작용을 하지 않았으나 구리(I)화합물, Cu(I)LOTf (OTf=trifluoromethanesulfonate)는 시클로프로판 생성물 trans:cis의 비율에 있어 80:20 이상의 높은 regioselectivity를 보였다.

Keywords

Acknowledgement

Supported by : 한국학술진흥재단

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