• Title/Summary/Keyword: Chiral catalyst

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Asymmetric Michael Addition of Ketones to Nitroolefins Catalyzed by a New Chiral Catalyst

  • Wang, Lian-Jun;Hu, Feng-Feng
    • Bulletin of the Korean Chemical Society
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    • v.31 no.5
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    • pp.1280-1282
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    • 2010
  • A new chiral catalyst was synthesized and found that it could catalyzed the asymmetric Michael reaction of ketones with nitroolefins smoothly at room temperature, giving the desired adducts in 71 - 92% yields with excellent diastereoselectivities and high enantioselectivities (up to 95% ee).

A New Approch for Catalyst Optimization: Host/Guest Complexes of Chiral Bisphosphine Bearing Imidazolidinone and Their Application in Rh-Catalyzed Asymmetric Hydrogenation

  • Park, Jung-Hwan;Shin, Hyun-Ik;Park, Doo-Han;Lee, Sang-Gi
    • Bulletin of the Korean Chemical Society
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    • v.31 no.3
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    • pp.635-638
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    • 2010
  • As a new strategy for the optimization of a chiral catalyst, the catalytic activity of the host-guest complexes of chiral bisphosphine bearing imidazolidinone was investigated in Rh-catalyzed asymmetric hydrogenation of enamide. Marginal enhancement in enantioselectivity was observed and the nature of interaction between host-guest was experimentally elucidated.

Chiral Resolution Using Enzymes (효소를 이용한 광학분할)

  • 이은교;정봉현
    • KSBB Journal
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    • v.15 no.5
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    • pp.415-422
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    • 2000
  • Enzymatic resolution is becoming increasingly important in the production of optically active pharmaceutical drugs and is now challenging the traditional synthetic methods for production of a variety of chiral intermediates and products. This article reviews the recent advances in chirotechnology using enzymes as a catalyst to resolve chiral compounds. The review focuses on the recent trends in chirotechnology and the application of enzymes to the production of industrially valuable pharmaceutical drugs.

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Synthesis of New Bimetallic Chiral Salen Catalyst Bearing Co(BF4)2 Salt and Its Application in Asymmetric Ring Opening of Epoxide

  • Kim, Yong-Suk;Lee, Choong-Young;Kim, Geon-Joong
    • Bulletin of the Korean Chemical Society
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    • v.31 no.10
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    • pp.2973-2979
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    • 2010
  • The newly synthesized homogeneous chiral Co(III) salen complexes were anchored non-covalently on the acidic sites of mesoporous Al-SBA-15. The Bronsted and Lewis acidic sites are attributed to the immobilization of fluorine functionalized chiral salen complexes on the supports. XRD, BET, TEM, FT-IR and ESCA (XPS) analyses were performed to characterize the property of support, and the structure of new homogeneous and heterogeneous chiral Co salen catalyst. The homogeneous and heterogeneous catalysts could be applied in asymmetric ring opening of epichlorohydrine (ECH) by water. They showed very high enantioselectivity and a good yield up to 99% in the catalytic synthesis of optically active products.

Synthesis of Optically Active Monoesters via Kinetic Resolution by Chiral Co (Salen) Complex Immobilized on Mesoporous BEA (메조세공 BEA에 고정화된 키랄 Co살렌 착체의 동적분할을 통한 고광학순도의 키랄 모노에스테르 합성)

  • Choi, Seong Dae;Park, Geun Woo;Lee, Gyung Chan;Kim, Geon-Joong
    • Applied Chemistry for Engineering
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    • v.26 no.2
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    • pp.132-137
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    • 2015
  • BEA-zeolite was modified by alkaline solution to introduce mesoporosity in the crystals and the homogeneous chiral Co(III) salen was immobilized in the mesopores. The dinuclear chiral Co(salen)-$GaCl_3$ catalyst immobilized on mesoporous BEA-zeolite showed high activity for the regioselective ring opening of terminal epoxides by carboxylic acids. Various chiral monoester derivatives could be synthesized with moderate enantioselectivity (47~69 ee%) from racemic epoxides through above reaction. When the chiral (S)-ECH was used as a reactant, it was efficiently resolved by carboxylic acid with a high enantioselectivity in the presence of heterogenized chiral salen catalyst, and the ring opened product afforded optically pure monoester epoxide (R)-GB (up to 98 ee%) through the ring closing in the basic solution by elimination of HCl. The heterogeneous catalyst could be fabricated easily, and the catalytic activity was retained for several times reuse without any further regeneration step.

Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to Benzylidenemalonitriles

  • Suh, Chang Won;Kim, Dae Young
    • Bulletin of the Korean Chemical Society
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    • v.35 no.1
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    • pp.98-102
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    • 2014
  • The organocatalytic enantioselective Michael addition reaction promoted by chiral binaphthyl-modified squaramide catalyst have been developed, allowing facile synthesis of the corresponding chiral 2-amino-4H-chromenes derivatives with excellent enantioselectivity (up to 99% ee). The method reported represents a practical entry for the preparation of chiral 2-amino-4H-chromenes derivatives.

Phase Transfer Catalyst (PTC) Catalyzed Alkylations of Glycinamides for Asymmetric Syntheses of $\alpha$-Amino Acid Derivatives

  • Park, Seon Yeong;Kim, Hyeon Ju;Im, Dong Yeol
    • Bulletin of the Korean Chemical Society
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    • v.22 no.9
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    • pp.958-962
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    • 2001
  • The chiral amine auxiliary mediated stereoselective alkylation reactions of glycinamides 1-6 and 15-17 using phase transfer catalyst (PTC) for liquid-solid extraction are described. The secondary N-(diphenylmethylene) glycinamides 1, 2 and 3 give better selectivities and yields than tertiary N-(diphenylmethylene) glycinamides 4, 5 and 6. Alkylation of the glycinamide 1 and 2 using 18-Crown-6 as a PTC in toluene at $-40^{\circ}C$ gives best selectivities and yields. Alkylations of N-(4-chlorophenylmethylene)glycinamides 15, 16 and 17 under same PTC conditions give $\alpha$, $\alpha-disubstituted$ amino acid derivatives 18, 19 and 20 with low diastereoselectivities.