고체 담체에 고정화된 키랄리간드의 비대칭 촉매반응에의 응용

이광연; 카테카라울; 김건중; Kwang-Yeon Lee; Rahul B. Kawthekar; Geon-Joong Kim

Journal of the Korean Industrial and Engineering Chemistry, Vol.17, No.6, 565-574, December, 2006

Export Citation

고체 담체에 고정화된 키랄리간드의 비대칭 촉매반응에의 응용

Application of Chiral Ligands Heterogenized over Solid Supports on Enantioselective Catalysis

이광연, 카테카라울, 김건중 ^†

인하대학교 생명화학공학부

Kwang-Yeon Lee, Rahul B. Kawthekar, and Geon-Joong Kim^†

Department of Chemical Engineering, Inha university, Incheon 402-751, Korea

E-mail:

초록

광학순도가 높은 이성체의 응용은 최근 들어 크게 증가되고 있는 추세이다. 여러 가지 방법 중에서도 비대칭 촉매합성반응을 통하여 선택적으로 순수한 광학이성체를 합성하는 것이 가장 매력적인 방법이다. 특히 키랄화합물을 합성하는 비대칭촉매반응에 있어서는 가격이 비싼 촉매를 소량 사용하면서도 활성이나 광학선택성 및 촉매수명을 높이도록 하는 조건이 매우 중요하게 대두된다. 활성이 큰 키랄촉매를 고정화시키면 반응 후에 반응혼합물을 여과법으로 쉽게 제거할 수 있다는 등의 취급상 용이한 점을 제공한다. 키랄촉매반응에서 생성물의 광학선택성을 향상시키고 여러 번 촉매를 재사용할 수 있도록 하려는 다양한 방법이 연구되고 있다. 본 총설에서는 여러 종류의 광학선택적인 불균일촉매에 관한 연구의 현황과 제한점 등을 주로 다루었다.

The trend towards the application of single enantiomers of chiral compounds is undoubtedly increasing. Among the various methods to obtain one single enantio-riched compound selectively, enantioselective catalysis is the most attractive method. Especially, it is important to increase the activity, selectivity and lifetime of usually expensive chiral catalysts with a minute quantity in the enantioselective synthesis. Immobilization of active homogeneous catalysts is a fashionable topic in asymmetric catalysis, providing the inherent advantage of easy separation and better handling properties. Many different ways have been investigated to improve the enantioselectivity of products and to recycle the catalysts. This review mainly focused on the present scope and limitations of different types of enantioselective heterogeneous catalysts.

Keywords:Immobilization;enantioselectivity;catalysis;chiral compound

[References]

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Sheldon RA, Chirotechnology; Industrial Synthesis of Optical Active Compounds, Marcel Dekker, New York (1994)
Blaser HU, Pugin B, Studer M, Chiral Catalyst Immobilization and Recycling, ed. D. E. De Vos, I. F. J. Vankelecom and P. A. Jacobs, WILEY-VCH, chap 1,2 (1998)
Tai A, Sugimura T, Chiral Catalyst Immobilization and Recycling, ed. D. E. De Vos, I. F. J. Vankelecom and P. A. Jacobs, WILEY-VCH, chap 8, 173 (1998)
Blaser HU, Wiehl HPJ, J. Mol. Catal, 215 (1991)
Minder B, Schurch M, Mallat T, Baiker A, Heinz T, Pfaltz A, J. Catal., 160(2), 261 (1996)
Minder B, Mallat T, Baiker A, Wang G, Heinz T, Pfaltz A, J. Catal., 154(2), 371 (1995)
Blaser HU, Pugin B, Chiral Reactions in Heterogeneous Catalysis, ed. G. Jannes and V. Dubois, Plenum Press, 33 (1995)
Bhaduri S, Darshane VS, Sharma K, Mukesh D, J. Chem. Soc. Chem. Commun., 1738 (1992)
Augustin RL, Heterogeneous Catalysis for the Synthetic Chemist, ed. Marcell Dekker, 313 (1996)
Balazsik K, Torok B, Szakonyi G, Bartok M, Appl. Catal. A: Gen., 182(1), 53 (1999)
Corma A, Iglesias M, del Pino C, Sanchez F, J. Chem. Soc. Chem. Commun., 1253 (1991)
Nagel U, Kinzel E, J. Chem. Soc. Chem. Commun., 1098 (1986)
Shephard DS, Stud. Surf. Sci. Catal., 129, 797 (2000)
Pini D, Mandoli A, Orlandi S, Salvadori P, Tetrahedron: Asymmetry, 10, 3883 (1999)
Kim GJ, Shin JH, Tetrahedron Lett., 40, 6827 (1999)
Sherrington DC, Catal. Today, 57(1-2), 87 (2000)
Canali L, Cowan E, Deleuze H, Gibson CL, Sherrington DC, Chem. Commun., 23, 2561 (1998)
Brunel D, Sutra P, Fajula F, Stud. Surf. Sci. Catal., 129, 773 (2000)
Xiang S, Zhang Y, Xin Q, Li C, Angew. Chem.-Int. Edit., 41, 821 (2002)
Song CE, Yang JW, Ha HJ, Tetrahedron: Asymmetry, 8, 841 (1997)
Bolm C, Gerlach A, Eur. J. Org. Chem., 21 (1998)
Lohray BB, Nandanan E, Bhushan V, Tetrahedron Lett., 35, 6559 (1994)
Song CE, Yang JW, Ha HJ, Lee SG, Tetrahedron: Asymmetry, 7, 645 (1996)
Kragl U, Dwars T, Trends Biotechnol., 19, 442 (2001)
Brunel D, Bellocq N, Sutra P, Cauvel A, Lasperas M, Moreau P, Renzo FD, Galarneau A, Fajula F, Coord. Chem. Rev., 178, 1085 (1998)
Kim SW, Bae SJ, Hyeon T, Kim BM, Microporous Mesoporous Mater., 44, 523 (2001)
Heckel A, Seebach D, Angew. Chem.-Int. Edit. Engl., 39, 163 (2000)
Sabater MJ, Corma A, Domenech A, Fornes V, Garcia H, Chem. Commun., 1285 (1997)
Ogunwumi SB, Bein T, Chem. Commun., 901 (1997)
Schuster C, Holderich WF, Catal. Today, 60(3-4), 193 (2000)
Frunza L, Kosslick H, Landmesser H, Hoft E, Fricke R, J. Mol. Catal. A-Chem., 123, 179 (1997)
Piaggio P, Mcmorn P, Langham C, Bethell D, Bulman-Page PC, Hancock FE, Hutchings GJ, New J. Chem., 1167 (1998)
Wagner HH, Hausmann H, Holderich WF, J. Catal., 203(1), 150 (2001)
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Franot C, Stone GB, Engeli P, Spondlin C, Waldvogel E, Tetrahedron: Asymmetry, 6, 2755 (1995)
Itsuno S, Sakurai Y, Ito K, Polymer, 28, 1005 (1987)

[Related Articles]

[1] Noyori R, Asymmetric Catalysis in Organic Synthesis, John Wiely, New York (1994)

[2] Sheldon RA, Chirotechnology; Industrial Synthesis of Optical Active Compounds, Marcel Dekker, New York (1994)

[3] Blaser HU, Pugin B, Studer M, Chiral Catalyst Immobilization and Recycling, ed. D. E. De Vos, I. F. J. Vankelecom and P. A. Jacobs, WILEY-VCH, chap 1,2 (1998)

[4] Tai A, Sugimura T, Chiral Catalyst Immobilization and Recycling, ed. D. E. De Vos, I. F. J. Vankelecom and P. A. Jacobs, WILEY-VCH, chap 8, 173 (1998)

[5] Blaser HU, Wiehl HPJ, J. Mol. Catal, 215 (1991)

[6] Minder B, Schurch M, Mallat T, Baiker A, Heinz T, Pfaltz A, J. Catal., 160(2), 261 (1996)

[7] Minder B, Mallat T, Baiker A, Wang G, Heinz T, Pfaltz A, J. Catal., 154(2), 371 (1995)

[8] Blaser HU, Pugin B, Chiral Reactions in Heterogeneous Catalysis, ed. G. Jannes and V. Dubois, Plenum Press, 33 (1995)

[9] Bhaduri S, Darshane VS, Sharma K, Mukesh D, J. Chem. Soc. Chem. Commun., 1738 (1992)

[10] Augustin RL, Heterogeneous Catalysis for the Synthetic Chemist, ed. Marcell Dekker, 313 (1996)

[11] Balazsik K, Torok B, Szakonyi G, Bartok M, Appl. Catal. A: Gen., 182(1), 53 (1999)

[12] Corma A, Iglesias M, del Pino C, Sanchez F, J. Chem. Soc. Chem. Commun., 1253 (1991)

[13] Nagel U, Kinzel E, J. Chem. Soc. Chem. Commun., 1098 (1986)

[14] Shephard DS, Stud. Surf. Sci. Catal., 129, 797 (2000)

[15] Pini D, Mandoli A, Orlandi S, Salvadori P, Tetrahedron: Asymmetry, 10, 3883 (1999)

[16] Kim GJ, Shin JH, Tetrahedron Lett., 40, 6827 (1999)

[17] Sherrington DC, Catal. Today, 57(1-2), 87 (2000)

[18] Canali L, Cowan E, Deleuze H, Gibson CL, Sherrington DC, Chem. Commun., 23, 2561 (1998)

[19] Brunel D, Sutra P, Fajula F, Stud. Surf. Sci. Catal., 129, 773 (2000)

[20] Xiang S, Zhang Y, Xin Q, Li C, Angew. Chem.-Int. Edit., 41, 821 (2002)

[21] Song CE, Yang JW, Ha HJ, Tetrahedron: Asymmetry, 8, 841 (1997)

[22] Bolm C, Gerlach A, Eur. J. Org. Chem., 21 (1998)

[23] Lohray BB, Nandanan E, Bhushan V, Tetrahedron Lett., 35, 6559 (1994)

[24] Song CE, Yang JW, Ha HJ, Lee SG, Tetrahedron: Asymmetry, 7, 645 (1996)

[25] Kragl U, Dwars T, Trends Biotechnol., 19, 442 (2001)

[26] Brunel D, Bellocq N, Sutra P, Cauvel A, Lasperas M, Moreau P, Renzo FD, Galarneau A, Fajula F, Coord. Chem. Rev., 178, 1085 (1998)

[27] Kim SW, Bae SJ, Hyeon T, Kim BM, Microporous Mesoporous Mater., 44, 523 (2001)

[28] Heckel A, Seebach D, Angew. Chem.-Int. Edit. Engl., 39, 163 (2000)

[29] Sabater MJ, Corma A, Domenech A, Fornes V, Garcia H, Chem. Commun., 1285 (1997)

[30] Ogunwumi SB, Bein T, Chem. Commun., 901 (1997)

[31] Schuster C, Holderich WF, Catal. Today, 60(3-4), 193 (2000)

[32] Frunza L, Kosslick H, Landmesser H, Hoft E, Fricke R, J. Mol. Catal. A-Chem., 123, 179 (1997)

[33] Piaggio P, Mcmorn P, Langham C, Bethell D, Bulman-Page PC, Hancock FE, Hutchings GJ, New J. Chem., 1167 (1998)

[34] Wagner HH, Hausmann H, Holderich WF, J. Catal., 203(1), 150 (2001)

[35] Itsuno S, Sakakura M, Ito K, J. Org. Chem., 55, 6047 (1990)

[36] Franot C, Stone GB, Engeli P, Spondlin C, Waldvogel E, Tetrahedron: Asymmetry, 6, 2755 (1995)

[37] Itsuno S, Sakurai Y, Ito K, Polymer, 28, 1005 (1987)